CN112898574A - Preparation method of organic silicon resin - Google Patents
Preparation method of organic silicon resin Download PDFInfo
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- CN112898574A CN112898574A CN202110357633.8A CN202110357633A CN112898574A CN 112898574 A CN112898574 A CN 112898574A CN 202110357633 A CN202110357633 A CN 202110357633A CN 112898574 A CN112898574 A CN 112898574A
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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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/44—Block-or graft-polymers containing polysiloxane sequences containing only polysiloxane sequences
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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
- C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
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Abstract
The invention relates to the technical field of preparation of silicone resin, and discloses a preparation method of organic silicon resin, which comprises the following steps: s1 adding cyclosiloxane and phenylcyclosiloxane to a reactor, and heating to remove water; s2, adding an initiator, an accelerator, a terminating agent and an anhydrous solvent into the reactor in S1 for reaction, and removing the anhydrous solvent after the reaction is finished to obtain a prepolymer containing vinyl; s3, adding the prepolymer in S2, a platinum catalyst, hydrogen-containing polysiloxane and fluorine-containing allyl ether into an anhydrous solvent for reaction, and removing the solvent after the reaction is finished to obtain the organic silicon resin. According to the preparation method, the organic silicon resin prepared by adopting a stepwise polymerization mode is good in compatibility with a resin matrix and good in dispersibility.
Description
Technical Field
The invention belongs to the technical field of silicone resin, and particularly relates to a preparation method of organic silicon resin.
Background
Organosilicon, i.e., organosilicon compounds, are compounds which contain Si-C bonds and have at least one organic group directly bonded to the silicon atom, and compounds in which organic groups are bonded to the silicon atom via oxygen, sulfur, nitrogen, or the like are also conventionally used as organosilicon compounds. Among them, the polysiloxane having a siloxane bond (-Si-O-Si-) as a skeleton is the most abundant, most studied and most widely used class of organosilicon compounds, and accounts for about 90% or more of the total amount.
The organic silicon has unique structure, has 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 high and low temperature resistance, electrical insulation, oxidation resistance stability, weather resistance, flame retardancy, hydrophobicity, corrosion resistance, no toxicity, no odor, physiological inertia and the like, is widely applied to the industries of aerospace, electronics and electricity, construction, transportation, chemical industry, textile, food, light industry, medical treatment and the like, and is mainly applied to sealing, adhesion, lubrication, coating, surface activity, demolding, defoaming, foam inhibition, water prevention, moisture prevention, inert filling and the like. With the continuous increase of the quantity and varieties of organic silicon, the application field is continuously widened, a unique important product system in the new chemical material field is formed, and a plurality of varieties are indispensable and cannot be replaced by other chemicals.
The organic silicon can be classified into silicone oil, silicone resin and silicone rubber according to chemical structure and performance. The silicone resin can be used as an elastomer or a functional assistant and added into a high polymer material matrix to improve the toughness, surface smoothness, wear resistance, scratch resistance and other properties of the material, but the silicone has lower surface energy, poor compatibility with most resins and poor dispersibility in the resins, so that the application of the silicone resin is limited.
Therefore, it is important to develop a silicone resin having good compatibility with a polymer resin.
Disclosure of Invention
< problems to be solved by the present invention >
The current silicone resin has poor compatibility with high molecular resin and poor dispersion effect, so that the application of the silicone resin is limited.
< technical solution adopted in the present invention >
In view of the above technical problems, an object of the present invention is to provide a method for preparing a silicone resin.
The specific contents are as follows:
the invention provides a preparation method of organic silicon resin, which comprises the following steps:
s1 adding cyclosiloxane and phenylcyclosiloxane to a reactor, and heating to remove water;
s2, adding an initiator, an accelerator and a terminating agent into the reactor in S1 for reaction, and removing the solvent after the reaction is finished to obtain a prepolymer containing vinyl;
s3, adding the prepolymer in S2, a platinum catalyst, hydrogen-containing polysiloxane and fluorine-containing allyl ether into an anhydrous solvent for reaction, and removing the solvent after the reaction is finished to obtain the organic silicon resin.
< advantageous effects achieved by the present invention >
(1) According to the invention, a segmented polymerization mode is adopted, the polysiloxane macromolecular prepolymer is prepared firstly, and then the ultrahigh molecular weight polysiloxane with the core-shell structure is prepared through hydrosilylation, no special equipment is needed in the preparation process, the energy consumption is low, the reaction control is simple, and the industrialization is easy to realize.
(2) According to the invention, the polysiloxane prepolymer containing vinyl, hydrogen-containing siloxane and a platinum catalyst are subjected to a hydrosilylation reaction to form the polysiloxane with a core-shell structure, so that the compatibility of the organic silicon resin and the high polymer resin is favorably improved, and the dispersibility of the organic silicon resin in a resin matrix is improved.
(3) According to the invention, phenyl cyclosiloxane and cyclosiloxane are subjected to ring opening and then subjected to copolymerization reaction, and the phenyl cyclosiloxane has the function of stabilizing free radicals, so that the residual free radicals under the conditions of high temperature and irradiation can be promoted, and the stability of the phenyl cyclosiloxane and the cyclosiloxane is promoted; meanwhile, the introduction of phenyl can also improve the low temperature resistance of the organic silicon resin.
(4) According to the invention, linear polysiloxane is prepared through a cyclosiloxane ring-opening reaction, and the side chain of the organic silicon resin is substituted with a heteroatom through the fluorination of the linear polysiloxane and fluorine-containing allyl ether, so that the solvent resistance and compressibility of the organic silicon resin are improved.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The invention provides a preparation method of organic silicon resin, which comprises the following steps:
s1 adding cyclosiloxane and phenylcyclosiloxane to a reactor, and heating to remove water;
s2, adding an initiator, an accelerator and a terminating agent into the reactor in S1 for reaction, and removing the solvent after the reaction is finished to obtain a prepolymer containing vinyl;
s3, adding the prepolymer in S2, a platinum catalyst, hydrogen-containing polysiloxane and fluorine-containing allyl ether into an anhydrous solvent for reaction, and removing the solvent after the reaction is finished to obtain the organic silicon resin.
The silicone resin comprises, by weight, 51-99 parts of cyclosiloxane, 1-49 parts of phenylcyclosiloxane, 0.01-1 part of initiator, 0-1 part of accelerator, 0.05-5 parts of end-capping agent, 0.5-20 ppm (calculated by metal platinum) of platinum catalyst, 1-15 parts of hydrogen-containing polysiloxane and 5-10 parts of fluorine-containing allyl ether.
In the hydrogen-containing polysiloxane of the present invention, in S1, the cyclosiloxane includes hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, or octaethylcyclotetrasiloxane, the phenylcyclosiloxane is methylphenylcyclosiloxane, and the methylphenylcyclosiloxane includes one or more of trimethyltriphenylcyclotrisiloxane, tetramethyltetraphenylcyclotetrasiloxane, and pentamethylpentaphenylcyclopentasiloxane.
In the present invention, in S2, the end-capping agent includes at least one of vinylpentamethyldisiloxane, divinyltetramethyldisiloxane, tetravinyldimethyldisiloxane, or dimethylvinylethoxysilane.
In the invention, in S3, the molecular weight of the hydrogenpolysiloxane is 500-10000.
In the present invention, in S3, the fluorine-containing allyl ether includes perfluoro (methallyl) ether, perfluoro (ethyl allyl) ether, perfluoro (n-propyl allyl) ether, perfluoro-2-propoxypropyl allyl ether, perfluoro-3-methoxy-n-propyl allyl ether, perfluoro-2-methoxy-ethyl allyl ether, or perfluoro-methoxy-methallyl ether.
In the present invention, in S2, the initiator is an alkali metal silanolate, and the accelerator includes tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide, hexamethylphosphoric triamide, or N-methylpyrrolidone.
In the present invention, in S1, heating is performed at 50 to 90 ℃.
In the present invention, N in S22And under the atmosphere, the reaction temperature is 90-130 ℃, and the reaction time is 25-40 h.
In the present invention, N in S32And under the atmosphere, the reaction temperature is 90-110 ℃, and the reaction time is 15-24 h.
In the present invention, the anhydrous solvent is at least one of benzene, toluene, tetrahydrofuran, dichloromethane, dioxane, n-hexane, cyclohexane, petroleum ether, n-heptane, and n-pentane.
< example >
Example 1
The organic silicon resin comprises the following raw materials:
75 parts of octamethylcyclotetrasiloxane, 25 parts of trimethyltriphenylcyclotrisiloxane, 0.5 part of silanol sodium salt, 0.2 part of N-methylpyrrolidone, 2 parts of divinyltetramethyldisiloxane, 15ppm of platinum catalyst, 10 parts of hydrogen-containing polysiloxane with the molecular weight of 1000 and 8 parts of perfluoro (methallyl) ether.
The preparation method of the organic silicon resin comprises the following steps:
s1, adding octamethylcyclotetrasiloxane and trimethyltriphenylcyclotrisiloxane into a reactor, heating to remove moisture, wherein the heating temperature is 60 ℃;
s2, dissolving sodium silanol, N-methyl pyrrolidone and divinyl tetramethyl disiloxane in toluene, adding the mixture into a reactor in S1 for reaction, and removing the toluene after the reaction is finished to obtain a prepolymer containing vinyl; n is a radical of2The reaction temperature is 110 ℃ and the reaction time is 40h under the atmosphere.
S3, adding the prepolymer in S2, a platinum catalyst, hydrogen-containing polysiloxane and perfluoro (methallyl) ether into toluene for reaction, and removing the toluene after the reaction is finished to obtain the organic silicon resin. N is a radical of2The reaction temperature is 100 ℃ and the reaction time is 15h under the atmosphere.
Example 2
The organic silicon resin comprises the following raw materials:
55 parts of octamethylcyclotetrasiloxane, 45 parts of trimethyltriphenylcyclotrisiloxane, 0.02 part of sodium silanol, 0.08 part of N-methylpyrrolidone, 0.1 part of divinyltetramethyldisiloxane, 5ppm of platinum catalyst, 5 parts of hydrogen-containing polysiloxane with the molecular weight of 1000 and 5 parts of perfluoro (methallyl) ether.
The preparation method of the organic silicon resin comprises the following steps:
s1, adding octamethylcyclotetrasiloxane and trimethyltriphenylcyclotrisiloxane into a reactor, heating to remove moisture, wherein the heating temperature is 60 ℃;
s2, dissolving sodium silanol, N-methyl pyrrolidone and divinyl tetramethyl disiloxane in tetrahydrofuran, adding into a reactor in S1 for reaction, and removing tetrahydrofuran after the reaction is finished to obtain a prepolymer containing vinyl; n is a radical of2The reaction temperature is 110 ℃ and the reaction time is 40h under the atmosphere.
S3, adding the prepolymer in S2, a platinum catalyst, hydrogen-containing polysiloxane and perfluoro (methallyl) ether into toluene for reaction, and removing tetrahydrofuran after the reaction is finished to obtain the organic silicon resin. N is a radical of2The reaction temperature is 130 ℃ and the reaction time is 40h under the atmosphere.
Example 3
The organic silicon resin comprises the following raw materials:
95 parts of octamethylcyclotetrasiloxane, 5 parts of trimethyltriphenylcyclotrisiloxane, 0.1 part of sodium silanol, 0.8 part of N-methylpyrrolidone, 5 parts of divinyltetramethyldisiloxane, 20ppm of platinum catalyst, 15 parts of hydrogen-containing polysiloxane with the molecular weight of 1000 and 10 parts of perfluoro (methallyl) ether.
The preparation method of the organic silicon resin comprises the following steps:
s1, adding octamethylcyclotetrasiloxane and trimethyltriphenylcyclotrisiloxane into a reactor, heating to remove moisture, wherein the heating temperature is 60 ℃;
s2, dissolving sodium silanol, N-methyl pyrrolidone and divinyl tetramethyl disiloxane in tetrahydrofuran, adding into a reactor in S1 for reaction, and removing tetrahydrofuran after the reaction is finished to obtain a prepolymer containing vinyl; n is a radical of2The reaction temperature is 110 ℃ and the reaction time is 40h under the atmosphere.
S3, adding the prepolymer in S2, a platinum catalyst, hydrogen-containing polysiloxane and perfluoro (methallyl) ether into toluene for reaction, and removing tetrahydrofuran after the reaction is finished to obtain the organic silicon resin. N is a radical of2The reaction temperature is 90 ℃ and the reaction time is 24h under the atmosphere.
Example 4
This example differs from example 1 in that sodium silanol is replaced by a barium silanol salt.
< comparative example >
Comparative example 1
This comparative example differs from example 1 in that no perfluoro (methallyl) ether is added.
< test example >
The following tests were carried out on the influence of the core-shell structure silicone resins prepared in examples 1 to 3 and comparative example 1 on the performance of the silicone encapsulating material for LED (light emitting element), and the test results are shown in table 1.
TABLE 1 Effect of core-shell mechanism Silicone resin on LED encapsulation Material Performance
Silicone resin | Tensile Strength (MPa) | Elongation at Break (%) | Hardness (A) |
Comparative example 1 | 4.2 | 98 | 65 |
Example 1 | 5.9 | 117 | 87 |
Example 2 | 5.2 | 110 | 78 |
Example 3 | 4.9 | 105 | 73 |
From the experimental results of table 1, it is known that the silicone resin prepared in the examples can improve the compatibility with the resin matrix, and the hardness and tensile properties thereof.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A preparation method of a silicone resin is characterized by comprising the following steps:
s1 adding cyclosiloxane and phenylcyclosiloxane to a reactor, and heating to remove water;
s2, adding an initiator, an accelerator, a terminating agent and an anhydrous solvent into the reactor in S1 for reaction, and removing the anhydrous solvent after the reaction is finished to obtain a prepolymer containing vinyl;
s3, adding the prepolymer in S2, a platinum catalyst, hydrogen-containing polysiloxane and fluorine-containing allyl ether into an anhydrous solvent for reaction, and removing the solvent after the reaction is finished to obtain the organic silicon resin.
2. The method for preparing the silicone resin according to claim 1, wherein the raw materials of the silicone resin comprise, by weight, 51 to 99 parts of cyclosiloxane, 1 to 49 parts of phenylcyclosiloxane, 0.01 to 1 part of initiator, 0 to 1 part of accelerator, 0.05 to 5 parts of blocking agent, 1 to 15 parts of hydrogen-containing polysiloxane, 5 to 10 parts of fluorine-containing allyl ether, and 0.5 to 20ppm (calculated as metal platinum) of platinum catalyst based on the total weight of the raw materials of the silicone resin.
3. The method according to claim 1, wherein in S1, the cyclosiloxane includes hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane, or octaethylcyclotetrasiloxane, the phenylcyclosiloxane is methylphenylcyclosiloxane, and the methylphenylcyclosiloxane includes at least one of trimethyltriphenylcyclotrisiloxane, tetramethyltetraphenylcyclotetrasiloxane, or pentamethylpentaphenylcyclopentasiloxane.
4. The method according to claim 1, wherein the end-capping agent in S2 comprises at least one of vinylpentamethyldisiloxane, divinyltetramethyldisiloxane, tetravinyldimethyldisiloxane, or dimethylvinylethoxysilane.
5. The method according to claim 1, wherein the hydrogenpolysiloxane has a molecular weight of 500 to 10000 in S3.
6. The method according to claim 1 or 2, wherein the fluorine-containing allyl ether in S3 comprises perfluoro (methallyl) ether, perfluoro (ethyl allyl) ether, perfluoro (n-propyl allyl) ether, perfluoro-2-propoxypropyl allyl ether, perfluoro-3-methoxy-n-propyl allyl ether, perfluoro-2-methoxy-ethyl allyl ether, or perfluoro-methoxy-methyl allyl ether.
7. The method according to claim 1 or 2, wherein in S2, the initiator is an alkali metal silanolate, and the accelerator comprises tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, triethylene glycol dimethyl ether, dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide, hexamethylphosphoric triamide, or N-methylpyrrolidone.
8. The method for producing a silicone resin according to claim 1, wherein S1 is heated at 50 to 90 ℃.
9. The method for producing a silicone resin according to claim 1 or 2, wherein in S2, N is2And under the atmosphere, the reaction temperature is 90-130 ℃, and the reaction time is 25-40 h.
10. The method for producing a silicone resin according to claim 1 or 2, wherein in S3, N is2Under the atmosphere, the reaction temperature is 90-110 ℃, and the reaction time is15~24h。
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CN115678012A (en) * | 2022-11-01 | 2023-02-03 | 中科院广州化学有限公司 | Multi-terminal alkylene branched polysiloxane and preparation method and application thereof |
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