CN113773501A - Preparation method of curable silicon-based hybrid resin - Google Patents
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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
- 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
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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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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Abstract
The invention relates to the field of silicon-based resin, in particular to a preparation method of curable silicon-based hybrid resin. By selecting the amino-terminated linear polysiloxane with specific molecular weight, firstly, diisocyanate is used for introducing reactive groups, and then the reaction product of diallyl isocyanurate and isocyanatopropyltriethoxysilane is introduced for toughening and simultaneously photo-curable double bonds are introduced, so that the cured product has excellent adhesiveness, and has the advantages of high surface drying speed, high hardness, good mechanical property, good salt spray resistance and the like. Can be widely applied to the field of outdoor super weather resistance, hydrophobic and oleophobic property, easy cleaning and protection.
Description
Technical Field
The present invention relates to the field of silicon-based resins, and in particular, to a method for preparing a curable silicon-based hybrid resin.
Background
With the research on silicones, more and more products are being designed. Chinese patent CN105008432B discloses a moisture-curable silicone adhesive composition comprising (a) a reactive resin, (B) a reactive polymer, (C) a moisture-curing catalyst, and (D) a crosslinker resin. The reactive resin (A) contains a compound containing R3SiO1/2Unit and SiO4/2A reaction product of an alkenyl-functional siloxane resin of units and an alkoxysilane-functional organosiloxane compound having at least one silicon-bonded hydrogen atom reacted in the presence of a hydrosilylation catalyst. The reactive polymer (B) comprises the reaction product of an alkoxysilane-functional organosiloxane compound having at least one silicon-bonded hydrogen atom and a polyorganosiloxane having an average of at least 2 aliphatically unsaturated organic groups per molecule reacted in the presence of a hydrosilylation catalyst. The organic silicon resin obtained in the patent is used for preparing hot melt adhesiveThe mechanical property, hardness and product state of the mixture can not meet the requirements of various scenes.
Disclosure of Invention
The invention aims to overcome the defects in the prior art and provide a preparation method of the curable silicon-based hybrid resin, and the curable silicon-based hybrid resin prepared by the method has excellent adhesive force on glass, metal, stone, ceramic, plastic, composite materials and the like, has high surface drying speed, high hardness and good toughness, and can be widely applied to the field of outdoor super-weather resistance, hydrophobic and oleophobic property and easy cleaning protection.
In order to achieve the purpose, the invention adopts the following technical scheme:
in one aspect, the present invention provides a method for preparing a curable silicon-based hybrid resin, comprising the steps of:
step one, adding amino-terminated linear polysiloxane with the number average molecular weight of 2000-6000 into a three-neck flask, performing vacuum dehydration for 1-2h at 110 ℃, introducing nitrogen, dropwise adding diisocyanate while stirring, and obtaining an intermediate product I after the reaction is finished;
adding diallyl isocyanurate into a three-neck flask, introducing nitrogen, heating for melting, dropwise adding isocyanatopropyl triethoxysilane while stirring, and obtaining an intermediate product II after the reaction is finished;
step three, uniformly mixing the intermediate product I, the intermediate product II and the photoinitiator according to the mass ratio of 80-90:10-20:1-5 to obtain the curable silicon-based hybrid resin;
in the first step, the molar ratio of amino groups to isocyanate groups is 1: 1.05-1.25;
in the second step, the molar ratio of the diallyl isocyanurate to the isocyanatopropyl triethoxysilane is 1: 0.95-1.05.
In one embodiment, the amino terminated linear polysiloxane is amino terminated polydimethylsiloxane having a molecular weight of 4000.
In one embodiment, the diisocyanate is one or more of toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate.
In one embodiment, the molar ratio of amino groups to isocyanate groups in step one is 1: 1.10.
In one embodiment, the molar ratio of diallyl isocyanurate to isocyanatopropyl triethoxysilane in step two is 1:1.
In one embodiment, the mass ratio of intermediate I, intermediate II and photoinitiator is 90:10: 3.
In one embodiment, the photoinitiator is one or more of TPO, TPO-L, 1173.
In another aspect, the present invention also provides a curable silicon-based hybrid resin prepared by the above method.
On the other hand, the invention also provides application of the curable silicon-based hybrid resin in a silicon-based sealing material, a silicon-based coating and a silicon-based adhesive.
On the other hand, the invention also provides application of the curable silicon-based hybrid resin in the water resistance, moisture resistance, weather resistance and stain resistance of a circuit board and a substrate surface.
According to the invention, by selecting the amino-terminated linear polysiloxane with a specific molecular weight, firstly, diisocyanate is used to introduce a reactive group, and then a reaction product of diallyl isocyanurate and isocyanatopropyltriethoxysilane is introduced to toughen and simultaneously introduce light-curable double bonds, so that the cured product has excellent adhesiveness, and has the advantages of high surface drying speed, high hardness, good mechanical property, good salt spray resistance and the like.
Detailed Description
In order to make the technical problems, technical solutions and advantageous effects to be solved by the present invention more clearly apparent, the present invention is further described in detail below with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The invention is described in further detail with reference to a number of tests performed in sequence, and a part of the test results are used as reference, and the following detailed description is given with reference to specific examples.
Example 1
The preparation method of the curable silicon-based hybrid resin comprises the following steps:
adding amino-terminated linear polysiloxane with the number average molecular weight of 4000 into a three-neck flask, performing vacuum dehydration for 1h at 110 ℃, introducing nitrogen, dropwise adding hexamethylene diisocyanate while stirring, and obtaining an intermediate product I after the reaction is finished;
adding diallyl isocyanurate into a three-neck flask, introducing nitrogen, heating for melting, dropwise adding isocyanatopropyl triethoxysilane while stirring, and obtaining an intermediate product II after the reaction is finished;
step three, uniformly mixing the intermediate product I, the intermediate product II and the photoinitiator TPO according to the mass ratio of 90:10:3 to obtain the curable silicon-based hybrid resin;
in the first step, the molar ratio of amino groups to isocyanate groups is 1: 1.1;
in the second step, the molar ratio of the diallyl isocyanurate to the isocyanatopropyl triethoxysilane is 1:1.
Example 2
The preparation method of the curable silicon-based hybrid resin comprises the following steps:
adding amino-terminated linear polysiloxane with the number average molecular weight of 2000 into a three-neck flask, performing vacuum dehydration for 1h at 110 ℃, introducing nitrogen, dropwise adding toluene diisocyanate while stirring, and obtaining an intermediate product I after the reaction is finished;
adding diallyl isocyanurate into a three-neck flask, introducing nitrogen, heating for melting, dropwise adding isocyanatopropyl triethoxysilane while stirring, and obtaining an intermediate product II after the reaction is finished;
step three, uniformly mixing the intermediate product I, the intermediate product II and a photoinitiator TPO-L according to a mass ratio of 80:20:1 to obtain the curable silicon-based hybrid resin;
in the first step, the molar ratio of amino groups to isocyanate groups is 1: 1.05;
in the second step, the molar ratio of the diallyl isocyanurate to the isocyanatopropyl triethoxysilane is 1: 0.95.
Example 3
The preparation method of the curable silicon-based hybrid resin comprises the following steps:
adding amino-terminated linear polysiloxane with the number average molecular weight of 6000 into a three-neck flask, dehydrating for 1h in vacuum at 110 ℃, introducing nitrogen, dropwise adding isophorone diisocyanate while stirring, and obtaining an intermediate product I after the reaction is finished;
adding diallyl isocyanurate into a three-neck flask, introducing nitrogen, heating for melting, dropwise adding isocyanatopropyl triethoxysilane while stirring, and obtaining an intermediate product II after the reaction is finished;
step three, uniformly mixing the intermediate product I, the intermediate product II and the photoinitiator 1173 according to the mass ratio of 90:10:5 to obtain the curable silicon-based hybrid resin;
in the first step, the molar ratio of amino groups to isocyanate groups is 1: 1.25;
in the second step, the molar ratio of the diallyl isocyanurate to the isocyanatopropyl triethoxysilane is 1: 1.05.
Example 4
The preparation method of the curable silicon-based hybrid resin comprises the following steps:
adding amino-terminated linear polysiloxane with the number average molecular weight of 4000 into a three-neck flask, dehydrating for 1h in vacuum at 110 ℃, introducing nitrogen, dropwise adding a mixture of hexamethylene diisocyanate and isophorone diisocyanate while stirring, and obtaining an intermediate product I after the reaction is finished;
adding diallyl isocyanurate into a three-neck flask, introducing nitrogen, heating for melting, dropwise adding isocyanatopropyl triethoxysilane while stirring, and obtaining an intermediate product II after the reaction is finished;
step three, uniformly mixing the intermediate product I, the intermediate product II and the photoinitiator TPO according to the mass ratio of 90:10:3 to obtain the curable silicon-based hybrid resin;
in the first step, the molar ratio of amino groups to isocyanate groups is 1:1.1, and the molar ratio of isophorone diisocyanate to hexamethylene diisocyanate is 1: 1;
in the second step, the molar ratio of the diallyl isocyanurate to the isocyanatopropyl triethoxysilane is 1:1.
Example 5
The preparation method of the curable silicon-based hybrid resin comprises the following steps:
adding amino-terminated linear polysiloxane with the number average molecular weight of 4000 into a three-neck flask, performing vacuum dehydration for 2 hours at the temperature of 110 ℃, introducing nitrogen, dropwise adding a mixture of hexamethylene diisocyanate and toluene diisocyanate while stirring, and obtaining an intermediate product I after the reaction is finished;
adding diallyl isocyanurate into a three-neck flask, introducing nitrogen, heating for melting, dropwise adding isocyanatopropyl triethoxysilane while stirring, and obtaining an intermediate product II after the reaction is finished;
step three, uniformly mixing the intermediate product I, the intermediate product II and the photoinitiator TPO according to the mass ratio of 85:15:3 to obtain the curable silicon-based hybrid resin;
in the first step, the molar ratio of amino groups to isocyanate groups is 1:1.25, and the molar ratio of hexamethylene diisocyanate to toluene diisocyanate is 1: 1;
in the second step, the molar ratio of the diallyl isocyanurate to the isocyanatopropyl triethoxysilane is 1: 0.95.
TABLE 1 curable silicon-based hybrid resin product parameters
The prepared curable silicon-based hybrid resin is sealed and stored at room temperature in a dark place, is prevented from contacting with water, acid and alkali, and can be packaged by a metal barrel.
The curable silicon-based hybrid resins prepared in examples 1 to 5 can be used as they are or after adjusting the viscosity using an appropriate amount of organic solvent.
The curable silicon-based hybrid resins prepared in examples 1 to 5 were respectively coated directly on a ceramic substrate, cured for 16 hours in an indoor environment at 25 ℃ and 50% relative humidity, irradiated for 10 minutes with an ultraviolet lamp, and then cured for 16 hours under the above conditions to obtain cured sample strips, which were tested according to the corresponding national and industrial standards, such as surface drying time (GB/T13477), adhesion (GB/T5210-85), hardness (GB/T6739), tear strength (GB/T528), and salt spray resistance (GB/T1771).
TABLE 2 comparison of Properties of curable silicon-based hybrid resins
As shown in Table 2, the curable silicon-based hybrid resin provided by the invention has excellent adhesiveness, and has the advantages of high surface drying speed, high hardness, good mechanical property, good salt spray resistance and the like, and particularly, the performance of the formula in example 2 is beyond expectations. The curable silicon-based hybrid resin is also an excellent long-acting low-surface-energy resin, and can be widely applied to the field of outdoor super-water-resistant, hydrophobic, oleophobic and easy-to-clean protection.
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 and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (10)
1. A method for preparing a curable silicon-based hybrid resin, comprising the steps of:
step one, adding amino-terminated linear polysiloxane with the number average molecular weight of 2000-6000 into a three-neck flask, performing vacuum dehydration for 1-2h at 110 ℃, introducing nitrogen, dropwise adding diisocyanate while stirring, and obtaining an intermediate product I after the reaction is finished;
adding diallyl isocyanurate into a three-neck flask, introducing nitrogen, heating for melting, dropwise adding isocyanatopropyl triethoxysilane while stirring, and obtaining an intermediate product II after the reaction is finished;
step three, uniformly mixing the intermediate product I, the intermediate product II and the photoinitiator according to the mass ratio of about 80-90:10-20:1-5 to obtain the curable silicon-based hybrid resin;
in the first step, the molar ratio of amino groups to isocyanate groups is about 1: 1.05-1.25;
in the second step, the molar ratio of the diallyl isocyanurate to the isocyanatopropyl triethoxysilane is about 1: 0.95-1.05.
2. The method according to claim 1, wherein the amino group-terminated linear polysiloxane is an amino-terminated polydimethylsiloxane having a molecular weight of 4000.
3. The method according to claim 1, wherein the diisocyanate is one or more of toluene diisocyanate, hexamethylene diisocyanate, isophorone diisocyanate, and toluene diamine.
4. The method according to claim 1, wherein the molar ratio of the amino group to the isocyanate group in the first step is 1: 1.10.
5. The method according to claim 1, wherein the molar ratio of diallyl isocyanurate to isocyanatopropyltriethoxysilane in step two is 1:1.
6. The method according to claim 1, wherein the mass ratio of the intermediate product I, the intermediate product II and the photoinitiator is 90:10: 3.
7. The method of claim 1, wherein the photoinitiator is one or more of TPO, TPO-L, 1173.
8. A curable silicon-based hybrid resin, which is obtained by the production method according to any one of claims 1 to 7.
9. Use of the curable silicon-based hybrid resin of claim 8 in silicon-based sealing materials, silicon-based coatings, and silicon-based adhesives.
10. Use of the curable silicon-based hybrid resin of claim 8 for waterproofing, moisture proofing, and weather and stain proofing of substrate surfaces of circuit boards.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114133572A (en) * | 2022-01-06 | 2022-03-04 | 江南大学 | Photosensitive organic silicon resin, preparation method and application |
| CN117844098A (en) * | 2024-03-07 | 2024-04-09 | 比音勒芬服饰股份有限公司 | Lightweight high-elastic environment-friendly leisure shoe midsole and preparation process thereof |
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| CN117844098A (en) * | 2024-03-07 | 2024-04-09 | 比音勒芬服饰股份有限公司 | Lightweight high-elastic environment-friendly leisure shoe midsole and preparation process thereof |
| CN117844098B (en) * | 2024-03-07 | 2024-04-30 | 比音勒芬服饰股份有限公司 | Lightweight high-elastic environment-friendly leisure shoe midsole and preparation process thereof |
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