CN111234234A - UV/moisture dual-curing polysiloxane and preparation method and application thereof - Google Patents
UV/moisture dual-curing polysiloxane and preparation method and application thereof Download PDFInfo
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- CN111234234A CN111234234A CN201811448810.8A CN201811448810A CN111234234A CN 111234234 A CN111234234 A CN 111234234A CN 201811448810 A CN201811448810 A CN 201811448810A CN 111234234 A CN111234234 A CN 111234234A
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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
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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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/10—Transparent films; Clear coatings; Transparent materials
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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
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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Abstract
The invention provides UV/moisture dual-curing polysiloxane, a preparation method and application thereof, and the UV/moisture dual-curing polysiloxane is linear polysiloxane with a side chain containing an epoxy group and an end group containing an alkoxy group and an acrylate group. The polymer has epoxy groups in side chains to increase the adhesion to a substrate, alkoxy groups and acryloyl groups in end groups to perform moisture and ultraviolet dual curing, and the polymer with lower viscosity can be used as a diluent and an adhesion promoter of high-viscosity UV/moisture dual-curing polysiloxane.
Description
Technical Field
The invention relates to polysiloxane capable of being cured by UV/moisture and a preparation method and application thereof, in particular to polysiloxane capable of being cured by two with low viscosity and a preparation method and application thereof, belonging to the field of silicon materials.
Background
The unique molecular structure of the organic silicon enables the organic silicon to have the performances of inorganic materials and organic materials, has the basic properties of low surface tension, small viscosity-temperature coefficient, high compressibility, high gas permeability and the like, has the excellent characteristics of oxidation resistance, stability, weather resistance, flame retardancy, hydrophobicity, corrosion resistance, physiological inertia and the like, and is applied to the industries of buildings, transportation, chemical industry, textile, food, light industry, medical treatment and the like. Particularly, the high and low temperature resistance and the dielectric property are widely applied to the protection of electronic circuit boards and main parts along with the development of the electronic industry.
The ultraviolet curing technology has the characteristics of fast curing, energy conservation, normal-temperature curing, less pollution, excellent performance and the like, and is a new-generation green chemical technology. The organic silicon polysiloxane molecular chain is introduced with a group with photosensitivity, so that the organic silicon polysiloxane molecular chain becomes the photo-curable polysiloxane, the curing efficiency can be greatly improved, the energy is saved, and the pollution to the environment can be reduced. The combination of the organic silicon material and the photocuring greatly expands the application field and the product variety of the organic silicon material.
The organic silicon type ultraviolet curing material is not suitable for adding a large amount of non-bulk resin due to the particularity of the formula, so that the adjustability of the formula is greatly reduced, and the improvement of the adhesive force of the organic silicon material to a base material is not facilitated. The application of ultraviolet curing technology in the electronic and electrical industry, especially the application of protective coatings, is often used together with the spraying process, which requires that the photo-cured silicone material should have a low viscosity for the spraying process to use.
Disclosure of Invention
The invention aims to overcome the characteristics that the existing organic silicon photocuring material has too high viscosity and is not suitable for a spraying process and cannot meet the requirement of high adhesion of a base material. The polymer can be used as an additive of similar high-viscosity materials, and can effectively reduce the viscosity of the product.
The technical scheme of the invention is as follows: a low viscosity UV/moisture dual curable polysiloxane having the formula:
wherein R is1Is composed of
R2Is composed of
R3is-OCH3or-OC2H5or-OC3H7Degree of polymerization n1And n2Each independently 10 to 100, n1And n2Same or different, preferably n1Is equal to n2And is 50-80.
The low viscosity UV/moisture dual curable polysiloxanes of the present invention have low viscosities of less than 200cP, preferably 115-142 cP.
The invention also provides a preparation method of the dual-curing polysiloxane, which comprises the following steps:
(1) in the presence of catalyst and polymerization inhibitor, N2Reacting the hydroxyl-terminated polysiloxane and the chain extender under the condition;
(2) adding an end-capping reagent for reaction, adding a neutralizing agent to inactivate the catalyst, removing low-boiling-point substances, and filtering to obtain a product.
Further, the chain extender means 3- (2, 3-epoxypropyl) propylmethyldimethoxysilane or 3- (2, 3-epoxypropyl) propylmethyldiethoxysilane, preferably 3- (2, 3-epoxypropyl) propylmethyldimethoxysilane.
The catalyst is one or more of lithium hydroxide, lithium methoxide and n-butyllithium, preferably n-butyllithium, and is preferably used in the form of a methanol or hexane solution thereof.
The neutralizing agent is one or more of stearic acid, gaseous carbon dioxide and dry ice, preferably the dry ice.
The polymerization inhibitor is selected from one or more of N, N-diethylhydroxylamine, 2, 6-di-tert-butyl-4-methylphenol (BHT), p-hydroxyphenol (MEHQ), phenothiazine and other commercial polymerization inhibitors, and N, N-diethylhydroxylamine is preferred.
Further, the reaction of step (1) is carried out at 50-70 ℃.
Further, the hydroxyl-terminated polysiloxane is 40 to 60 parts by mass, the chain extender is 2 to 8 parts by mass, preferably 3 to 5 parts by mass, the polymerization inhibitor is 0.0001 to 0.01 part by mass, preferably 0.001 to 0.005 part by mass, and the catalyst is 0.001 to 0.1 part by mass, preferably 0.01 to 0.08 part by mass.
Further, the end-capping agent is selected from the group consisting of acryloxypropyltrimethoxysilane, methacryloxypropyltrimethoxysilane, acryloxypropyltriethoxysilane, methacryloxypropyltriethoxysilane, methacryloxypropyltripropoxysilane, preferably acryloxypropyltrimethoxysilane, in an amount of 7 to 14 parts by mass, preferably 9 to 11 parts by mass.
Further, the amount of the neutralizing agent is 0.5 to 3 parts by mass, preferably 1 to 2 parts by mass.
The operating conditions for removing low boilers are 40-60 ℃ and 5-15mbar (absolute pressure).
The present invention further provides the use of the above-described UV/moisture dual-curable polysiloxane as a diluent and/or an adhesion promoter for a dual-curing type coating (UV/moisture dual-curable polysiloxane coating).
The invention has the beneficial effects that the structure of the polymer contains the acryloxy and the alkoxy, the ultraviolet/moisture dual curing can be realized, and meanwhile, the molecular structure contains the epoxy group, so that the adhesive force to a base material can be effectively improved. The polymer has low viscosity and good transparency, and can be used as a diluent and a tackifier of a dual-curing coating.
Detailed Description
The following examples are given for the purpose of further illustrating the invention and are not to be construed as limiting in practice.
Example 1
The chemical reaction process is as follows:
taking a 1000ml four-mouth flask, fully drying, adding 500g of low-viscosity hydroxyl-terminated polysiloxane, starting stirring for 300r/min, vacuumizing and dewatering for 60min at 70 ℃, cooling to 60 ℃, adding 40.7g of 3- (2, 3-epoxypropyl) propyl methyl dimethoxysilane, 0.05g N, N-diethylhydroxylamine and nitrogen atmosphere, stirring for 15min at 60 ℃, adding 1ml of N-butyllithium hexane solution (1.6M), reacting for 3h, adding 108.7g of acryloyloxypropyl trimethoxysilane, reacting for 2h, cooling to room temperature, adding 15g of dry ice for neutralization for 30min, removing low boiling at 50 ℃ under the condition of 10mbar, adding 10g of diatomite as a filter aid to obtain a product, performing positive pressure filtration to obtain 85.07% of a transparent product, wherein the viscosity of the product is 130 cP.
Example 2
The chemical reaction process is as follows
Taking 1000ml of a four-neck flask, fully drying, adding 500g of low-viscosity hydroxyl-terminated polysiloxane, starting stirring for 300r/min, vacuumizing and dewatering for 60min at 70 ℃, cooling to 60 ℃, adding 45.9g of 3- (2, 3-epoxypropyl) propyl methyldiethoxysilane, 0.05g N and N-diethylhydroxylamine, stirring for 15min at 60 ℃ in a nitrogen atmosphere, adding 1.5ml of N-butyl lithium hexane solution (1.6M), reacting for 4h, adding 108.7g of acryloyloxypropyl trimethoxysilane, reacting for 2h, cooling to room temperature, adding 15g of dry ice for neutralizing for 30min, removing low boiling water at 50 ℃ under the condition of 10mbar, adding 10g of diatomite as a filter aid, filtering under positive pressure to obtain 544.5g of transparent product, wherein the yield is 83.27%, and the viscosity of the product is 142 cP.
Example 3
Taking a 1000ml four-neck flask, fully drying, adding 500g of low-viscosity hydroxyl-terminated polysiloxane, starting stirring for 300r/min, vacuumizing and dewatering for 60min at 70 ℃, cooling to 60 ℃, adding 40.7g of 3- (2, 3-epoxypropyl) propyl methyldimethoxysilane and 0.05g of MEHQ, stirring for 15min at 60 ℃ in a nitrogen atmosphere, adding 1ml of n-butyllithium hexane solution, reacting for 3h, adding 115.7g of methacryloxypropyl trimethoxysilane, reacting for 2h, cooling to room temperature, adding 15g of dry ice for neutralizing for 30min, pumping out low boiling at 10mbar at 50 ℃, adding 10g of diatomite as a filter aid into the product, filtering under positive pressure to obtain 568.6g of transparent product, wherein the yield is 86.62%, and the viscosity of the product is 115 cP.
Example 4
Taking a 1000ml four-mouth flask, fully drying, adding 500g of low-viscosity hydroxyl-terminated polysiloxane, starting stirring for 300r/min, vacuumizing and dewatering for 60min at 80 ℃, cooling to 50 ℃, adding 40.7g of 3- (2, 3-epoxypropyl) propyl methyl dimethoxysilane, 0.05g N, N-diethylhydroxylamine, stirring for 15min at 50 ℃ in a nitrogen atmosphere, adding 1ml of N-butyllithium hexane solution, reacting for 2h, adding 128.7g of acryloyloxypropyl triethoxysilane, reacting for 3h, cooling to room temperature, adding 15g of dry ice for neutralization for 30min, removing low-boiling filter aid at 50 ℃ and 10mbar, adding 10g of diatomite to obtain a product, filtering at positive pressure to obtain 560.4g of a transparent product, wherein the yield is 86.30%, and the product viscosity is 120 cP.
Example 5
Taking a 1000ml four-mouth flask, fully drying, adding 500g of low-viscosity hydroxyl-terminated polysiloxane, starting stirring for 300r/min, vacuumizing at 80 ℃ for 60min, cooling to 45 ℃, adding 45.9g of 3- (2, 3-epoxypropyl) propyl methyldimethoxysilane and 0.05g of BHT, stirring at 45 ℃ for 15min in a nitrogen atmosphere, adding 1ml of n-butyl lithium hexane solution, reacting for 4h, adding 115.7g of acryloyloxypropyltrimethoxysilane, reacting for 4h, cooling to room temperature, adding 15g of dry ice, neutralizing for 30min, pumping out low boiling at 50 ℃ and 10mbar, adding 10g of diatomite as a filter aid into the product, filtering at positive pressure to obtain 570.2g of transparent product, wherein the yield is 87.80%, and the product viscosity is 130 cP.
Example 6
Taking a 1000ml four-neck flask, fully drying, adding 500g of low-viscosity hydroxyl-terminated polysiloxane, starting stirring for 300r/min, vacuumizing and dewatering for 60min at 80 ℃, cooling to 50 ℃, adding 40.7g of 3- (2, 3-epoxypropyl) propyl methyl dimethoxy silane, 0.05g N, N-diethylhydroxylamine, stirring for 15min at 50 ℃ in a nitrogen atmosphere, adding 1g of 5 wt% lithium hydroxide methanol solution, reacting for 3h, adding 108.7g of acryloyloxy propyl trimethoxy silane, reacting for 3h, cooling to room temperature, adding 10g of 5 wt% stearic acid methanol solution for neutralization for 30min, removing low boiling under the condition of 50 ℃ and 10mbar, adding 10g of diatomite as a filter aid, filtering under positive pressure to obtain 560.4g of transparent product, wherein the yield is 86.30%, and the viscosity of the product is 120 cP.
Application example 1
50g of the product obtained in example 1 was taken, 11730.5 g of photoinitiator and 0.3g of dibutyltin dilaurate were added, the mixture was stirred uniformly under a nitrogen atmosphere, 3g of the mixture was put into an ultraviolet curing oven to be cured for 30s, and then the mixture was placed in the air to be cured for 72h at room temperature, so that a transparent solid was obtained.
Application example 2
50g of the product obtained in example 1 was taken, 11730.5 g of photoinitiator and 0.3g of tetra-n-butyl titanate were added, the mixture was stirred uniformly under nitrogen atmosphere, 3g of the mixture was put into an ultraviolet curing oven to be cured for 30s, and then the mixture was placed in the air to be cured for 72h at room temperature, so that a pale yellow transparent solid was obtained.
Application example 3
50g of the product obtained in example 3 was taken, 11730.5 g of a photoinitiator and 0.3g of dibutyltin dilaurate were added, the mixture was stirred uniformly under a nitrogen atmosphere, 3g of the mixture was put into an ultraviolet curing oven to be cured for 180s, and then the mixture was placed in the air to be cured at room temperature for 72h, so that a transparent solid was obtained.
Application example 4
Taking 10g of the product obtained in the example 1 and 100g of hydroxyl-terminated silicone oil with the viscosity of 750cP, using three-dimensional dynamic mixing and mixing for 5min to obtain uniform and transparent liquid, wherein the viscosity of the product with the viscosity of 640Cp is reduced by 14.67%, taking 10g of the mixed liquid, centrifuging for 3 min at 2000r/min, and no layering phenomenon occurs. Transparent solids were likewise obtained using the method described in example 1.
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 invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (10)
1. A UV/moisture dual-curable polysiloxane, which has the following structural formula:
2. UV/moisture dual cure silicone according to claim 1, characterized in that it has a low viscosity of less than 200cP, preferably 115-142 cP.
3. The method for producing the dual-cure polysiloxane of claim 1 or 2, characterized by comprising the steps of:
(1) in the presence of a catalyst and a polymerization inhibitor, reacting hydroxyl-terminated polysiloxane and a chain extender under the condition of inert atmosphere;
(2) adding an end-capping reagent for reaction, adding a neutralizing agent to inactivate the catalyst, removing low-boiling-point substances, and filtering to obtain a product.
4. The process according to claim 3, wherein the chain extender is 3- (2, 3-epoxypropyl) propylmethyldimethoxysilane or 3- (2, 3-epoxypropyl) propylmethyldiethoxysilane, preferably 3- (2, 3-epoxypropyl) propylmethyldimethoxysilane.
5. The method according to claim 3 or 4, wherein the catalyst is one or more of lithium hydroxide, lithium methoxide, n-butyllithium, preferably n-butyllithium; and/or
The neutralizing agent is one or more of stearic acid, gaseous carbon dioxide and dry ice, preferably the dry ice; and/or
The polymerization inhibitor is selected from one or more of N, N-diethylhydroxylamine, 2, 6-di-tert-butyl-4-methylphenol (BHT), p-hydroxyphenol (MEHQ) and phenothiazine, and is preferably N, N-diethylhydroxylamine.
6. The production method according to any one of claims 3 to 5, wherein the reaction of step (1) is carried out at 50 to 70 ℃.
7. The production method according to any one of claims 3 to 6, wherein the hydroxyl-terminated polysiloxane is 40 to 60 parts by mass, the chain extender is 2 to 8 parts by mass, preferably 3 to 5 parts by mass, the polymerization inhibitor is 0.0001 to 0.01 part by mass, preferably 0.001 to 0.005 part by mass, and the catalyst is 0.001 to 0.1 part by mass, preferably 0.01 to 0.08 part by mass.
8. The method according to any one of claims 3 to 7, characterized in that the blocking agent is selected from the group consisting of acryloxypropyltrimethoxysilane, methacryloxypropyltrimethoxysilane, acryloxypropyltriethoxysilane, methacryloxypropyltriethoxysilane, methacryloxypropyltripropoxysilane, preferably acryloxypropyltrimethoxysilane, in an amount of 7 to 14 parts by mass, preferably 9 to 11 parts by mass.
9. The production method according to any one of claims 3 to 8, wherein the neutralizing agent is used in an amount of 0.5 to 3 parts by mass, preferably 1 to 2 parts by mass.
10. Use of the UV/moisture dual-curable polysiloxane according to claim 1 or 2 as a diluent and/or adhesion promoter for dual-curable coatings.
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| CN201811448810.8A CN111234234A (en) | 2018-11-28 | 2018-11-28 | UV/moisture dual-curing polysiloxane and preparation method and application thereof |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114196021A (en) * | 2022-01-06 | 2022-03-18 | 万华化学集团股份有限公司 | Anchoring agent and preparation method and application thereof |
| JP7408807B2 (en) | 2021-03-16 | 2024-01-05 | モメンティブ・パフォーマンス・マテリアルズ・コリア・カンパニー・リミテッド | Silicone composition and its cured product |
| TWI833458B (en) * | 2022-11-21 | 2024-02-21 | 長興材料工業股份有限公司 | Dual curable epoxy-terminated polysiloxane and preparation method and application thereof |
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| CN104193996A (en) * | 2014-08-21 | 2014-12-10 | 烟台德邦先进硅材料有限公司 | UV (ultraviolet)/moisture-curing organic silicon glue |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7408807B2 (en) | 2021-03-16 | 2024-01-05 | モメンティブ・パフォーマンス・マテリアルズ・コリア・カンパニー・リミテッド | Silicone composition and its cured product |
| CN114196021A (en) * | 2022-01-06 | 2022-03-18 | 万华化学集团股份有限公司 | Anchoring agent and preparation method and application thereof |
| TWI833458B (en) * | 2022-11-21 | 2024-02-21 | 長興材料工業股份有限公司 | Dual curable epoxy-terminated polysiloxane and preparation method and application thereof |
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