CN110790936A - Dual-curing organic silicon resin and preparation method thereof - Google Patents
Dual-curing organic silicon resin and preparation method thereof Download PDFInfo
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- 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
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- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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Abstract
The invention belongs to the field of new materials, and particularly relates to a dual-curing organic silicon resin and a preparation method thereof. The organic silicon resin not only effectively overcomes the defects of high curing temperature, long curing time, poor adhesion to a base layer, poor high-temperature mechanical strength and the like of the existing single organic silicon resin material, but also has the advantage of low viscosity, and can have great application potential in the field of solvent-free coatings.
Description
Technical Field
The invention belongs to the field of new materials, and particularly relates to a dual-curing organic silicon resin and a preparation method thereof.
Background
Polyorganosiloxanes have many unique properties, such as resistance to high and low temperatures, weathering, aging, electrical insulation, ozone, water, fire, physiological inertness, etc. These excellent properties of silicone products are incomparable and replaceable with other organic polymer materials. Therefore, the polymer material has been widely applied to the aspects of aerospace, electronics and electrical, light industry, chemical industry, textile, machinery, construction, transportation, medical treatment and health, agriculture, daily life of people and the like, and has become an important and indispensable novel polymer material in national economy.
However, silicone resin also has many disadvantages, such as poor adhesion due to low surface energy, poor mechanical properties such as tear resistance and impact resistance due to low intermolecular forces, and the like, which greatly limits its application range. In particular, in recent years, the requirements of electronic components on the performance of dielectric insulating materials are further improved, higher requirements on the comprehensive performance of silicone resin are provided, and the problems of further improvement and perfection of the electrical and mechanical properties of silicone resin are urgently solved.
As one of the most widely applied matrix resins in polymer composite materials, epoxy resin has excellent physical and mechanical properties, adhesive property, electrical insulation property and chemical stability, but epoxy resin also has the defects of high crosslinking density, large internal stress, large hygroscopicity, poor dimensional stability, low flexibility, poor dielectric property and the like caused by easy water absorption of hydroxyl in the structure, and the introduction of silicone resin can just make up the defects of the above properties and obtain epoxy modified silicone resin with high performance. The acrylic resin is synthesized by a series of acrylate monomers, wherein the acrylate monomers comprise a soft monomer, a hard monomer, a functional monomer and the like, different monomers respectively endow different performances to the polymer, and the acrylic resin required by experiments can be synthesized by adjusting the proportion of the monomers. The acrylic resin has the advantages of high transparency, attractive coating, high glossiness, high corrosion resistance, high adhesion and low cost, and has wide application prospect in modification of polysiloxane coatings.
In view of the defects of high curing temperature, long curing time, poor adhesion to a base layer, high-temperature mechanical strength and the like of the existing single organic silicon resin. Therefore, the preparation of the modified organic silicon resin with excellent performance and simple construction operation has important significance.
Disclosure of Invention
The invention aims to overcome the defects of high curing temperature, long curing time, poor adhesion to a base layer, low high-temperature mechanical strength and the like of the conventional organic silicon resin, and provides a dual-curing organic silicon resin and a preparation method thereof.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a dual-curing organic silicon resin has a structural formula as follows:
wherein: n is more than or equal to 5 and less than or equal to 10, x is more than or equal to 1 and less than or equal to 5, and y is more than or equal to 1 and less than or equal to 5; r1Is C6H11O3、C12H23O6、C15H29O6Or C5H9O4；R2Is C3H5O2、C2H4O、C17H24O、C2H4；R3Is H, CH3Or C3H7。
A dual-curing organic silicon resin and a preparation method thereof comprise the following steps:
step 1): carrying out hydrosilylation reaction on the trifunctional acrylate and the double-end-group hydrogenpolysiloxane to obtain trifunctional single-end-group hydrogenpolysiloxane marked as A;
step 2): the alkene containing epoxy group and A have hydrosilylation reaction, and the polysiloxane containing epoxy group is marked as B;
step 3): and (3) carrying out hydrosilylation reaction on the trifunctional acrylate and the B to obtain modified organic silicon resin which is marked as C.
All expressed as mole fraction of the reaction raw materials
Preferably, the step 1) is specifically:
dissolving 1 part of hydrogen-containing double-end siloxane in 80 parts of tetrahydrofuran, and mixing 0.3-0.4 part of trifunctional acrylate, 1 wt% of polymerization inhibitor and 10 parts of-5Dissolving the catalyst in 10 parts of tetrahydrofuran, adding the tetrahydrofuran into a constant-pressure dropping funnel, controlling the dropping speed, stirring, reacting at 70-120 ℃ for 4-5 hours, distilling under reduced pressure to remove the solvent, adding 50 parts of toluene, excessive sodium bicarbonate and 10 parts of deionized water, stirring at 60 ℃ for 3 hours, separating a water phase, taking an organic layer, distilling under reduced pressure to remove the solvent to obtain the trifunctional single-end hydrogenpolysiloxane, and marking as A;
the amount of the polymerization inhibitor is 1 wt% of the mass of the trifunctional acrylate.
Preferably, the step 2) is specifically:
dissolving 1 part of A in 80 parts of tetrahydrofuran, and mixing 2-2.1 parts of epoxy alkene, 1 wt% of polymerization inhibitor and 10 parts of-5Dissolving the catalyst in 10 parts of tetrahydrofuran, adding the tetrahydrofuran into a constant-pressure dropping funnel, controlling the dropping speed, stirring, reacting at 70-120 ℃ for 4-5 hours, distilling under reduced pressure to remove the solvent, adding 50 parts of toluene, excessive sodium bicarbonate and 10 parts of deionized water, stirring at 60 ℃ for 3 hours, separating a water phase, taking an organic layer, distilling under reduced pressure to remove the solvent to obtain the trifunctional single-end hydrogenpolysiloxane, and marking as B;
the amount of the polymerization inhibitor is 1 wt% of the mass of the epoxy alkene.
Preferably, the step 3) is specifically:
dissolving 1 part of B in 80 parts of tetrahydrofuran, and dissolving 1-1.2 parts of trifunctional acrylate, 1 wt% of polymerization inhibitor and 10 parts of-5Dissolving the catalyst in 10 parts of tetrahydrofuran, adding the tetrahydrofuran into a constant-pressure dropping funnel, controlling the dropping speed, stirring, reacting at 70-120 ℃ for 4-5 hours, distilling under reduced pressure to remove the solvent, adding 50 parts of toluene, excessive sodium bicarbonate and 10 parts of deionized water, stirring at 60 ℃ for 3 hours, separating a water phase, taking an organic layer, distilling under reduced pressure to remove the solvent to obtain a target product, and marking as C;
the amount of the polymerization inhibitor is 1 wt% of the mass of the trifunctional acrylate.
Preferably, the preparation method of the dual-curing organic silicon resin is characterized by comprising the following steps: the trifunctional acrylate is trimethylolpropane triacrylate, ethoxytrimethylolpropane triacrylate, propoxytrimethylolpropane triacrylate or pentaerythritol triacrylate.
Preferably, the preparation method of the dual-curing organic silicon resin is characterized by comprising the following steps: the epoxy alkene is glycidyl methacrylate, allyl glycidyl ether, cardanol glycidyl ether or 1, 2-epoxy-5-hexene.
Preferably, the preparation method of the dual-curing organic silicon resin is characterized by comprising the following steps: the catalyst is chloroplatinic acid, carbene alkane, platinum dioxide or aluminum trichloride.
Preferably, the preparation method of the dual-curing organic silicon resin is characterized by comprising the following steps: the polymerization inhibitor is 2, 6-di-tert-butyl-p-methylphenol, hydroquinone or p-hydroxyanisole.
A dual cure silicone coating, a UV cured coating thereof, characterized by: the composite material comprises the following raw materials in parts by weight:
80-90 parts of dual-curing organic silicon resin;
5-10 parts of tripropylene glycol diacrylate;
5-10 parts of butyl acrylate;
1841-5 parts of a photoinitiator;
and 2611-5 parts of photoinitiator.
Preferably, the preparation method of the UV-cured coating of the dual-cured silicone coating comprises the following steps:
(1) operating in a dark room, and mixing the dual-curing organic silicon resin, the photo-curing monomer diluent and the photoinitiator for 30min at room temperature to obtain a uniform mixture;
(2) mixing the mixture obtained in the step (1) to be uniform, stirring in vacuum to remove bubbles, coating the mixture on a tinplate, placing the tinplate in a UV curing box, and setting the curing energy to be 80-100W/cm2And irradiating the sample for 0.5-3min under the UV light at a distance of 10cm from the light source to prepare the UV-cured organic silicon coating.
A double-curing organic silicon coating is a double-component thermosetting coating, which is characterized in that: the composite material comprises the following raw materials in parts by weight:
100 parts of dual-curing organic silicon resin;
3-20 parts of amine epoxy curing agent with active hydrogen equivalent of 200 g/mol;
1-5 parts of thermal initiator BPO.
Preferably, the preparation method of the thermosetting coating of the dual-curing organic silicon coating comprises the following steps:
the dual-curing organic silicon resin and the amine epoxy curing agent with the equivalent of active hydrogen of 200g/mol are uniformly mixed, the paint is mixed to the sprayable viscosity, the mixture is sprayed on a tin plate, and the mixture is baked for 0.5 to 1 hour at the temperature of between 50 and 80 ℃ until the mixture is dried to obtain the thermosetting organic silicon coating.
The preparation process of the dual-curing organic silicon resin provided by the invention comprises the following steps:
the invention has the beneficial effects that:
(1) the invention provides a dual-curing organic silicon resin, which is prepared by taking double-end-group hydrogen-containing siloxane as a raw material through multi-step hydrosilylation reaction and the like through molecular design and adjustment of a polymer structure, overcomes the defects of high curing temperature, long curing time, poor adhesion to a base layer and poor high-temperature mechanical strength of the traditional organic silicon material, and simultaneously has wide sources of used raw materials and simple and safe operation in the whole reaction process.
(2) The invention provides a preparation method of dual-curing organic silicon resin, wherein a triacrylate monomer is used as one of raw materials, firstly, the triacrylate monomer provides a multi-functionality effect, and a branching reaction can be performed in the later period; secondly, the structure of the acrylate monomer provides the application of the acrylate monomer in UV curing; finally, the acrylate-modified structures have superior gloss to traditional silicones.
(3) The invention provides a preparation method of dual-curing organic silicon resin, which adopts epoxy monomer modification, and on one hand, epoxy groups provide adhesive force with base materials; on the other hand, the epoxy group as a reactive group can react with an active hydrogen group such as an amino group, a carboxyl group and the like, so that the effect of rapid curing is achieved.
(4) The invention provides a preparation method of dual-curing organic silicon resin, which adopts three-step reaction synthesis, wherein the reaction mechanism is hydrosilylation, the reaction operation process is simple, and the industrial production is convenient.
(5) The invention provides a dual-curing organic silicon resin, which is a photo-thermal dual-curing system by synthesizing an organic silicon material with an acrylate structure and an epoxy structure through molecular design and adjustment of a polymer structure, solves the defects of high curing temperature, long curing time, poor adhesion to a base layer and poor high-temperature mechanical strength of a single organic silicon material, can adjust the molecular weight and the structure, and has wide application in the fields of high solid content, low viscosity and no solvent.
The specific implementation mode is as follows:
the present invention will be described in detail with reference to examples. It is to be understood, however, that the following examples are illustrative of embodiments of the present invention and are not to be construed as limiting the scope of the invention.
Example 1
Step 1) dissolving 1 part of double-end hydrogen-containing siloxane in 80 parts of tetrahydrofuran, and dissolving 0.3 part of trimethylolpropane triacrylate, 1 wt% of 2, 6-di-tert-butyl-p-methylphenol, and 10 parts of tetrahydrofuran-5Dissolving chloroplatinic acid in 10 parts of tetrahydrofuran, adding into a constant pressure dropping funnel, controlling the dropping speed, stirring, reacting at 70 ℃ for 5 hours, distilling under reduced pressure to remove the solvent, adding 50 parts of toluene, excessive sodium bicarbonate and 10 parts of deionized water, stirring at 60 ℃ for 3 hours, separating the water phase, taking the organic layer, distilling under reduced pressure to remove the solvent to obtain the single-end-group hydrogen-containing polysiloxane (IR: 1640 cm)-1、811cm-1: -C ═ C — disappearance), noted a;
the using amount of the 2, 6-di-tert-butyl-p-methylphenol is 1 wt% of the mass of the trimethylolpropane triacrylate.
Step 2) dissolving 1 part of A in 80 parts of tetrahydrofuran, and dissolving 2.1 parts of glycidyl methacrylate, 1 wt% of 2, 6-di-tert-butyl-p-methylphenol and 10 parts of-5Dissolving chloroplatinic acid in 10 parts of tetrahydrofuran, adding into a constant pressure dropping funnel, controlling the dropping speed, stirring, reacting at 70 ℃ for 5 hours, distilling under reduced pressure to remove the solvent, adding 50 parts of toluene, excessive sodium bicarbonate and 10 parts of deionized water, stirring at 60 ℃ for 3 hours, separating the water phase, taking the organic layer, distilling under reduced pressure to remove the solvent to obtain the bifunctional epoxy-terminated hydrogenpolysiloxane (IR: 1640 cm)-1、811cm-1: -C ═ C — disappearance; 910cm-1: epoxy group present), as B;
the using amount of the 2, 6-di-tert-butyl-p-methylphenol is 1 wt% of the mass of the glycidyl methacrylate.
Step 3) dissolving 1 part of B in 80 parts of tetrahydrofuran,1.2 parts of trimethylolpropane triacrylate, 1 wt% of 2, 6-di-tert-butyl-p-methylphenol, 10-5Dissolving chloroplatinic acid in 10 parts of tetrahydrofuran, adding into a constant pressure dropping funnel, controlling the dropping speed, stirring, reacting at 70 ℃ for 5 hours, distilling under reduced pressure to remove the solvent, adding 50 parts of toluene, excessive sodium bicarbonate and 10 parts of deionized water, stirring at 60 ℃ for 3 hours, separating the water phase, taking the organic layer, distilling under reduced pressure to remove the solvent to obtain a target product (IR: 1633 cm)-1、810cm-1: -C ═ C-is present; 910cm-1: epoxy group present), noted C;
the using amount of the 2, 6-di-tert-butyl-p-methylphenol is 1 wt% of the mass of the trimethylolpropane triacrylate.
Examples 2-8, otherwise identical to example 1, differ as set forth in the following table:
the dual-curing silicone resin obtained in specific example 1 was used as a base material in application examples, and was formulated into a silicone coating material.
Application example 1
A UV curing coating of a dual-curing organic silicon coating comprises the following raw materials in parts by weight:
80 parts of dual-curing organic silicon resin;
10 parts of tripropylene glycol diacrylate;
10 parts of butyl acrylate;
1845 parts of a photoinitiator;
and 2611 part of photoinitiator.
The preparation steps of the UV curing coating are as follows:
(1) operating in a dark room, and mixing the dual-curing organic silicon resin, the photo-curing monomer diluent and the photoinitiator for 30min at room temperature to obtain a uniform mixture;
(2) mixing the mixture obtained in the step (1) to be uniform, stirring in vacuum to remove bubbles, coating the mixture on a tinplate, placing the tinplate in a UV curing box, and setting the curing energy to be 80W/cm2And irradiating the sample for 3min under the UV light at a distance of 10cm from the light source to prepare the UV-cured organic silicon coating.
Application examples 2 to 3 were the same as application example 1 except that the following table was used
Application example 4
A dual cure silicone coating, the thermal cure coating of which: the composite material comprises the following raw materials in parts by weight:
100 parts of dual-curing organic silicon resin;
20 parts of amine epoxy curing agent with active hydrogen equivalent of 200 g/mol;
and 5 parts of thermal initiator BPO.
The preparation steps of the thermosetting coating are as follows:
the dual-curing organic silicon resin and the amine epoxy curing agent with the equivalent of active hydrogen of 200g/mol are uniformly mixed, the paint is mixed to the sprayable viscosity, the mixture is sprayed on a tin plate, and the mixture is baked for 1 hour at 50 ℃ until the mixture is completely dried, so that the thermosetting organic silicon coating is obtained.
Application examples 5 to 6 were conducted in the same manner as in application example 4 except that the following Table was used
Application examples comparative examples 1 to 3 were compared with application example 1, except that:
practical example comparative example 1
A preparation method of an organic silicon coating comprises the following steps: the UV curing coating comprises the following raw materials in parts by weight:
80 parts of common organic silicon resin;
10 parts of tripropylene glycol diacrylate;
10 parts of butyl acrylate;
1845 parts of a photoinitiator;
and 2611 part of photoinitiator.
The preparation steps of the UV curing coating are as follows:
(1) operating in a dark room, and mixing the dual-curing organic silicon resin, the photo-curing monomer diluent and the photoinitiator for 30min at room temperature to obtain a uniform mixture;
(2) mixing the mixture obtained in the step (1) to be uniform, stirring in vacuum to remove bubbles, coating the mixture on a tinplate, placing the tinplate in a UV curing box, and setting the curing energy to be 80W/cm2And irradiating the sample for 3min under the UV light at a distance of 10cm from the light source to prepare the UV-cured organic silicon coating.
Comparative examples 2 to 3 were used and comparative example 1 was used in the same manner except as shown in the following table
Application examples comparative examples 4 to 6 were all compared with application example 4, except that:
practical example comparative example 4
A preparation method of an organic silicon coating comprises the following steps: the thermosetting coating comprises the following raw materials in parts by weight:
100 parts of common organic silicon resin;
20 parts of amine epoxy curing agent with active hydrogen equivalent of 200 g/mol;
and 5 parts of thermal initiator BPO.
The preparation steps of the thermosetting coating are as follows:
the dual-curing organic silicon resin and the amine epoxy curing agent with the equivalent of active hydrogen of 200g/mol are uniformly mixed, the paint is mixed to the sprayable viscosity, the mixture is sprayed on a tin plate, and the mixture is baked for 1 hour at 50 ℃ until the mixture is completely dried, so that the thermosetting organic silicon coating is obtained.
Comparative examples 5 to 6 were applied and comparative example 4 was otherwise applied, with the following differences:
the performance tests of the cured silicone resins prepared in practical examples 1-6 and practical examples 1-6 of the present invention on the formed paint films were respectively determined, and the test results are shown in Table 1
TABLE 1
The test method comprises the following steps:
1) film thickness: the film thickness was measured according to GB/T13452.2.
2) Pencil hardness: pencil hardness was measured according to GB/T6739-2006 standard.
3) Adhesion force: the adhesion of the coating was tested by cross-hatch according to GB/T9286-1998.
4) Gloss: the gloss of the coating was tested using a BYK micro gloss meter.
5) Gel content: sampling, crushing, extracting with acetone in a Soxhlet extractor for 24h, drying at 100 ℃ for 1h, weighing, and dividing the obtained mass by the original mass to obtain the gel content of the cured material.
6) Impact strength: the test was carried out according to the GB/T1732-93 standard.
In light of the foregoing description of the preferred embodiment of the present invention, many modifications and variations will be apparent to those skilled in the art without departing from the spirit and scope of the invention. The technical scope of the present invention is not limited to the content of the specification, and must be determined according to the scope of the claims.
Claims (9)
1. The dual-curing organic silicon resin is characterized by having a structural formula as follows:
wherein: n is more than or equal to 5 and less than or equal to 10, x is more than or equal to 1 and less than or equal to 5, and y is more than or equal to 1 and less than or equal to 5; r1Is C6H11O3、C12H23O6、C15H29O6Or C5H9O4；R2Is C3H5O2、C2H4O、C17H24O、C2H4；R3Is H, CH3Or C3H7。
2. A preparation method of a dual-curing organic silicon resin is characterized by comprising the following steps: all expressed as mole fraction of the reaction raw materials
Step 1): carrying out hydrosilylation reaction on the trifunctional acrylate and the double-end-group hydrogenpolysiloxane to obtain trifunctional single-end-group hydrogenpolysiloxane marked as A;
step 2): the alkene containing epoxy group and A have hydrosilylation reaction, and the polysiloxane containing epoxy group is marked as B;
step 3): and (3) carrying out hydrosilylation reaction on the trifunctional acrylate and the B to obtain modified organic silicon resin which is marked as C.
3. The method for preparing a dual-cure silicone resin according to claim 2, characterized in that: the step 1) is specifically as follows:
dissolving 1 part of hydrogen-containing double-end siloxane in 80 parts of tetrahydrofuran, and mixing 0.3-0.4 part of trifunctional acrylate, 1 wt% of polymerization inhibitor and 10 parts of-5Dissolving the catalyst in 10 parts of tetrahydrofuran, adding the tetrahydrofuran into a constant-pressure dropping funnel, controlling the dropping speed, stirring, reacting at 70-120 ℃ for 4-5 hours, distilling under reduced pressure to remove the solvent, adding 50 parts of toluene, excessive sodium bicarbonate and 10 parts of deionized water, stirring at 60 ℃ for 3 hours, separating a water phase, taking an organic layer, distilling under reduced pressure to remove the solvent to obtain the trifunctional single-end hydrogenpolysiloxane, and marking as A;
the amount of the polymerization inhibitor is 1 wt% of the mass of the trifunctional acrylate.
4. The method for preparing a dual-cure silicone resin according to claim 2, characterized in that: the step 2) is specifically as follows:
dissolving 1 part of A in 80 parts of tetrahydrofuran, and mixing 2-2.1 parts of epoxy alkene, 1 wt% of polymerization inhibitor and 10 parts of-5Dissolving the catalyst in 10 parts of tetrahydrofuran, adding the tetrahydrofuran into a constant-pressure dropping funnel, controlling the dropping speed, stirring, reacting at 70-120 ℃ for 4-5 hours, distilling under reduced pressure to remove the solvent, adding 50 parts of toluene, excessive sodium bicarbonate and 10 parts of deionized water, stirring at 60 ℃ for 3 hours, separating a water phase, taking an organic layer, distilling under reduced pressure to remove the solvent to obtain the trifunctional single-end hydrogenpolysiloxane, and marking as B;
the amount of the polymerization inhibitor is 1 wt% of the mass of the epoxy alkene.
5. The method for preparing a bis-crosslinked polythiourethane material according to claim 2, characterized in that: the step 3) is specifically as follows:
dissolving 1 part of B in 80 parts of tetrahydrofuran, and dissolving 1-1.2 parts of trifunctional acrylate, 1 wt% of polymerization inhibitor and 10 parts of-5Dissolving the catalyst in 10 parts of tetrahydrofuran, adding the tetrahydrofuran into a constant-pressure dropping funnel, controlling the dropping speed, stirring, reacting at 70-120 ℃ for 4-5 hours, distilling under reduced pressure to remove the solvent, adding 50 parts of toluene, excessive sodium bicarbonate and 10 parts of deionized water, stirring at 60 ℃ for 3 hours, separating a water phase, taking an organic layer, distilling under reduced pressure to remove the solvent to obtain a target product, and marking as C;
the amount of the polymerization inhibitor is 1 wt% of the mass of the trifunctional acrylate.
6. The method for producing a dual-cure silicone resin according to claim 3 or 5, characterized in that: the trifunctional acrylate is trimethylolpropane triacrylate, ethoxytrimethylolpropane triacrylate, propoxytrimethylolpropane triacrylate or pentaerythritol triacrylate.
7. The method for preparing a dual-cure silicone resin according to claim 4, characterized in that: the epoxy alkene is glycidyl methacrylate, allyl glycidyl ether, cardanol glycidyl ether or 1, 2-epoxy-5-hexene.
8. The method for producing a dual-cure silicone resin according to any one of claims 3, 4, or 5, characterized in that: the catalyst is chloroplatinic acid, carbene alkane, platinum dioxide or aluminum trichloride.
9. The method for producing a dual-cure silicone resin according to any one of claims 3, 4, or 5, characterized in that: the polymerization inhibitor is 2, 6-di-tert-butyl-p-methylphenol, hydroquinone or p-hydroxyanisole.
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| CN116063682A (en) * | 2022-12-07 | 2023-05-05 | 中科院广州化学有限公司 | UV/moisture dual-curing epoxy-based organic silicon resin and preparation method and application thereof |
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