CN111499877A - Preparation method of organic silicon modified epoxy resin - Google Patents
Preparation method of organic silicon modified epoxy resin Download PDFInfo
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- CN111499877A CN111499877A CN202010348640.7A CN202010348640A CN111499877A CN 111499877 A CN111499877 A CN 111499877A CN 202010348640 A CN202010348640 A CN 202010348640A CN 111499877 A CN111499877 A CN 111499877A
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Abstract
The invention discloses a preparation method of organosilicon modified epoxy resin, which comprises the following two steps: preparation of silicone oligomer: adding 30-40 parts of alkoxy silane monomer and 5-10 parts of solvent A into a reactor; stirring, heating, dropwise adding a mixed solution consisting of a catalyst A and distilled water, reacting for 2 hours, then distilling under reduced pressure, and filtering to obtain an organic silicon oligomer; preparing organic silicon modified epoxy resin: adding 5-10 parts of solvent B, 1-3 parts of catalyst B, 10-15 parts of prepared organic silicon oligomer and 40-50 parts of bisphenol A epoxy resin into a reactor, introducing nitrogen for protection, heating to 80 ℃ under the stirring state, reacting for 1-1.5h, reacting for 3-4h at 120 ℃, and then distilling under reduced pressure to obtain the organic silicon modified epoxy resin. The organosilicon modified epoxy resin prepared by the invention is prepared by introducing a flexible organosilicon chain segment into an epoxy resin molecule, has an epoxy group chain segment and a siloxane chain segment, and has the advantages of good flexibility, high temperature resistance, excellent corrosion resistance and low internal stress of a cured product.
Description
Technical Field
The invention relates to the technical field of chemical synthetic materials, in particular to a preparation method of organosilicon modified epoxy resin.
Background
Epoxy resin is an excellent thermosetting polymer material, has the advantages of excellent mechanical property, thermal property, chemical corrosion resistance and the like, and has the advantages of high bonding strength, low curing shrinkage rate and the like, but the epoxy resin also has certain limitations, such as poor flexibility, low temperature resistance and the like. Although the epoxy resin can be modified by physical or chemical methods, the overall performance of the modified epoxy resin can not meet the requirements of a more severe service environment.
The organic silicon resin is a polymer taking-Si-O-Si-as a molecular main chain, and has the characteristics of good heat resistance, water resistance, excellent electrical insulation, weather resistance and the like because the silicon-oxygen bond energy is higher than the carbon-carbon bond energy. However, silicone resins also suffer from significant drawbacks, typically high curing temperatures and long curing times, poor resistance of the coating to organic solvents, low adhesion, etc., which greatly limits their wide-range applications. Thereby limiting its application.
The organosilicon modified epoxy resin is an effective way which is developed in recent years and can reduce the internal stress of the epoxy resin and increase the toughness, high temperature resistance and other properties of the epoxy resin. At present, many researches on organosilicon modified epoxy resin are carried out at home and abroad, and the researches mainly comprise 4 types of reactions of active end groups, generation of block copolymers by using a silica coupling agent, substitution of partial siloxane side groups, preparation of polysiloxane particles in advance and the like. The main methods are blending and copolymerization. The blending modification of the polymer is to blend different kinds of polymers, and although the blending modification cost is low, the modification effect is not particularly ideal because the compatibility of the organosilicon polymer and the epoxy resin is poor.
Disclosure of Invention
The invention aims to provide a preparation method of organosilicon modified epoxy resin, which utilizes active end groups such as hydroxyl, amino and alkoxy on organosilicon to react with epoxy groups and hydroxyl in the epoxy resin to generate graft or block copolymer, thereby solving the problem of compatibility, and introducing stable and flexible silica chains into a curing structure to improve the fracture toughness of the epoxy resin.
In order to achieve the purpose, the technical scheme adopted by the invention is as follows:
a preparation method of organosilicon modified epoxy resin comprises the following steps:
step one, preparing organic silicon oligomer: according to the mass parts, 30-40 parts of alkoxy silane monomer and 5-10 parts of solvent A are added into a reactor provided with a heating, stirring and refluxing device; heating to 80 ℃ under a stirring state, beginning to dropwise add a mixed solution consisting of 2-5 parts of catalyst A and 20-30 parts of distilled water, controlling the dropwise adding time to be 1-1.5h, keeping the temperature to be 80-90 ℃ after the dropwise adding is finished, reacting for 2h, then distilling under reduced pressure for 0.5-1h, evaporating ethanol and part of solvent generated by the reaction, cooling to room temperature, and filtering to obtain the organic silicon oligomer with the ethoxy mass percent content of 5-10% and the solid mass percent content of more than 80%;
step two, preparing the organosilicon modified epoxy resin: according to the mass parts, 5-10 parts of solvent B, 1-3 parts of catalyst B, 10-15 parts of organic silicon oligomer prepared in the step one and 40-50 parts of bisphenol A epoxy resin are sequentially added into a reactor provided with a heating, stirring and refluxing device, nitrogen is introduced for protection, the temperature is raised to 80 ℃ under the stirring state for reaction for 1-1.5h, the temperature is raised to 120 ℃ for reaction for 3-4h, and then reduced pressure distillation is carried out for 0.5-1h, so as to prepare the organic silicon modified epoxy resin.
Preferably, the alkoxysilane monomer in step one is selected from compounds of the following general structural formula:
Y(4-n)Si(OR)n;
wherein Y represents a phenyl group or a primary or secondary alkyl group having 1 to 4 carbon atoms, R represents an alkyl group having 1 to 3 carbon atoms, and n is an integer of 1 to 4.
Preferably, the alkoxysilane monomer includes at least one of dimethyldiethoxysilane, monomethyltriethoxysilane, or diphenyldiethoxysilane.
Preferably, in the second step, the bisphenol A type epoxy resin is epoxy resin E-44 or epoxy resin E-51, and the epoxy value is 0.41-0.54mol/100 g.
Preferably, the catalyst A in the first step is hydrochloric acid or phosphoric acid.
Preferably, the catalyst B in the second step is at least one of dibutyl tin dilaurate or butyl titanate.
Preferably, the solvent methyl in the first step is at least one of xylene, butyl acetate or butanol.
Preferably, the solvent B in the second step is at least one of xylene and butanol.
The organosilicon modified epoxy resin prepared by the invention utilizes polysiloxane with alkoxy to carry out copolycondensation reaction with hydroxyl (-OH) in a bisphenol A epoxy resin molecular chain to generate ROH and form stable Si-O-R bonds. The main chemical reaction equation is as follows:
the organosilicon modified epoxy resin prepared by the invention is a modified polymer which is provided with an epoxy chain segment and a siloxane chain segment by introducing a flexible organosilicon chain segment into an epoxy resin molecule, and the flexibility, the temperature resistance and the corrosion resistance of the epoxy resin are improved and the internal stress of a cured product is reduced by the modification. Compared with epoxy resin, the tensile strength of the prepared organic silicon modified epoxy resin polymer is improved by 86%, and the temperature resistance is improved by 60 ℃.
Drawings
FIG. 1 is a block diagram of a process flow of an embodiment of the present invention.
Detailed Description
The present invention will be described in further detail with reference to the following drawings and specific examples.
Example 1
A preparation method of organosilicon modified epoxy resin comprises the following steps:
step one, preparing organic silicon oligomer: adding 6 parts of dimethyldiethoxysilane, 18 parts of monomethyltriethoxysilane, 6 parts of diphenyldiethoxysilane and 5 parts of xylene in parts by mass into a reactor equipped with a heating, stirring and refluxing device; heating to 80 ℃ under a stirring state, starting to dropwise add a mixed solution consisting of 2 parts of hydrochloric acid and 20 parts of distilled water, controlling the dropwise adding time to be 1h, keeping the temperature at 80-90 ℃ after the dropwise adding is finished, reacting for 2h, then distilling under reduced pressure for 0.5h, evaporating ethanol and part of solvent generated by the reaction, cooling to room temperature, and filtering to obtain the organic silicon oligomer with 5-10% of ethoxy content and more than 80% of solid content.
Step two, preparing the organosilicon modified epoxy resin: sequentially adding 5 parts of dimethylbenzene, 1 part of dibutyltin dilaurate, 10 parts of the organic silicon oligomer prepared in the first step and 40 parts of epoxy resin E-44 into a reactor provided with a heating, stirring and refluxing device in parts by mass, introducing nitrogen for protection, heating to 80 ℃ in a stirring state, reacting for 1 hour, reacting for 3 hours at 120 ℃, and then distilling under reduced pressure for 0.5 hour to obtain the organic silicon modified epoxy resin.
Example 2
A method for preparing organosilicon modified epoxy resin, the organosilicon modified epoxy resin comprises the following steps:
step one, preparing organic silicon oligomer: adding 10 parts of dimethyldiethoxysilane, 18 parts of monomethyltriethoxysilane, 12 parts of diphenyldiethoxysilane and 10 parts of xylene in parts by mass into a reactor equipped with a heating, stirring and refluxing device; heating to 80 ℃ under a stirring state, starting to dropwise add a mixed solution consisting of 5 parts of hydrochloric acid and 30 parts of distilled water, controlling the dropwise adding time to be 1.5h, keeping the temperature at 80-90 ℃ after the dropwise adding is finished, reacting for 2h, then distilling under reduced pressure for 1h, evaporating ethanol and part of solvent generated by the reaction, cooling to room temperature, and filtering to obtain the organic silicon oligomer with 5-10% of ethoxy content and more than 80% of solid content.
Step two, preparing the organosilicon modified epoxy resin: sequentially adding 10 parts by mass of xylene, 3 parts by mass of dibutyltin dilaurate, 10 parts by mass of the organosilicon oligomer prepared in the first step and 50 parts by mass of epoxy resin E-51 into a reactor provided with a heating, stirring and refluxing device, introducing nitrogen for protection, heating to 80 ℃ under a stirring state, reacting for 1.5h, reacting for 4h at 120 ℃, and then distilling under reduced pressure for 1h to obtain the organosilicon modified epoxy resin.
Example 3
A method for preparing organosilicon modified epoxy resin, the organosilicon modified epoxy resin comprises the following steps:
step one, preparing organic silicon oligomer: adding 18 parts of dimethyldiethoxysilane, 20 parts of monomethyltriethoxysilane and 6 parts of butyl acetate into a reactor which is provided with a heating, stirring and refluxing device according to parts by mass; heating to 80 ℃ under a stirring state, starting to dropwise add a mixed solution consisting of 3 parts of phosphoric acid and 25 parts of distilled water, controlling the dropwise adding time to be 1.7h, keeping the temperature at 80-90 ℃ after the dropwise adding is finished, reacting for 2h, then distilling under reduced pressure for 0.8h, evaporating ethanol and part of solvent generated by the reaction, cooling to room temperature, and filtering to obtain the organic silicon oligomer with the ethoxy content of 5-10% and the solid content of more than 80%.
Step two, preparing the organosilicon modified epoxy resin: according to the mass parts, 6 parts of butyl acetate, 2 parts of butyl titanate, 13 parts of the organic silicon oligomer prepared in the step one and 45 parts of epoxy resin E-44 are sequentially added into a reactor provided with a heating, stirring and refluxing device, nitrogen is introduced for protection, the temperature is raised to 80 ℃ under the stirring state for reaction for 1.3h, the temperature is raised to 120 ℃ for reaction for 3.5h, and then reduced pressure distillation is carried out for 0.7h, so as to prepare the organic silicon modified epoxy resin.
Example 4
A method for preparing organosilicon modified epoxy resin, the organosilicon modified epoxy resin comprises the following steps:
step one, preparing organic silicon oligomer: adding 8 parts of methyl triethoxysilane, 28 parts of diphenyl diethoxy silane, 5 parts of xylene and 3 parts of butanol into a reactor provided with a heating, stirring and refluxing device according to parts by mass; heating to 80 ℃ under a stirring state, starting to dropwise add a mixed solution consisting of 4 parts of phosphoric acid and 26 parts of distilled water, controlling the dropwise adding time to be 1.2h, keeping the temperature at 80-90 ℃ after the dropwise adding is finished, reacting for 2h, then distilling under reduced pressure for 0.9h, evaporating ethanol and part of solvent generated by the reaction, cooling to room temperature, and filtering to obtain the organic silicon oligomer with the ethoxy content of 5-10% and the solid content of more than 80%.
Step two, preparing the organosilicon modified epoxy resin: according to the mass parts, 5 parts of dimethylbenzene, 3 parts of butanol, 2.5 parts of butyl titanate, 0.2 part of dibutyl tin dilaurate, 11 parts of the organic silicon oligomer prepared in the step one and 270g of epoxy resin E-44 are sequentially added into a reactor provided with a heating, stirring and refluxing device, nitrogen is introduced for protection, the temperature is raised to 80 ℃ under the stirring state for reaction for 1.4h, the temperature is raised to 120 ℃ for reaction for 3.6h, and then reduced pressure distillation is carried out for 0.8h, so that the organic silicon modified epoxy resin is prepared.
Example 5
A method for preparing organosilicon modified epoxy resin, the organosilicon modified epoxy resin comprises the following steps:
step one, preparing organic silicon oligomer: adding 37 parts of dimethyldiethoxysilane and 6 parts of ethyl acetate into a reactor provided with a heating, stirring and refluxing device according to parts by mass; heating to 80 ℃ under a stirring state, starting to dropwise add a mixed solution consisting of 4 parts of hydrochloric acid and 26 parts of distilled water, controlling the dropwise adding time to be 1.4h, keeping the temperature at 80-90 ℃ after the dropwise adding is finished, reacting for 2h, then distilling under reduced pressure for 0.6h, evaporating ethanol and part of solvent generated by the reaction, cooling to room temperature, and filtering to obtain the organic silicon oligomer with the ethoxy content of 5-10% and the solid content of more than 80%.
Step two, preparing the organosilicon modified epoxy resin: according to the mass parts, 6 parts of ethyl acetate, 2 parts of dibutyl tin dilaurate, 13 parts of organic silicon oligomer prepared in the first step and 13 parts of epoxy resin E-5145 parts are sequentially added into a reactor provided with a heating, stirring and refluxing device, nitrogen is introduced for protection, the temperature is raised to 80 ℃ under the stirring state for reaction for 1.5h, the temperature is raised to 120 ℃ for reaction for 3.6h, and then reduced pressure distillation is carried out for 0.7h, so as to obtain the organic silicon modified epoxy resin.
Example 6
A method for preparing organosilicon modified epoxy resin, the organosilicon modified epoxy resin comprises the following steps:
step one, preparing organic silicon oligomer: adding 14 parts of dimethyldiethoxysilane, 17 parts of monomethyltriethoxysilane, 5 parts of diphenyldiethoxysilane and 8 parts of butanol into a reactor which is provided with a heating, stirring and refluxing device according to parts by mass; heating to 80 ℃ under a stirring state, starting to dropwise add a mixed solution consisting of 6 parts of phosphoric acid and 26 parts of distilled water, controlling the dropwise adding time to be 1.7h, keeping the temperature at 80-90 ℃ after the dropwise adding is finished, reacting for 2h, then distilling under reduced pressure for 0.8h, evaporating ethanol and part of solvent generated by the reaction, cooling to room temperature, and filtering to obtain the organic silicon oligomer with the ethoxy content of 5-10% and the solid content of more than 80%.
Step two, preparing the organosilicon modified epoxy resin: and (2) sequentially adding 8 parts of butanol, 2.6 parts of dibutyl tin dilaurate, 15 parts of the organic silicon oligomer prepared in the step one and the epoxy resin E-4448 parts into a reactor provided with a heating, stirring and refluxing device in parts by mass, introducing nitrogen for protection, heating to 80 ℃ under a stirring state, reacting for 1.5h, reacting for 3h at 120 ℃, and then distilling under reduced pressure for 0.5h to obtain the organic silicon modified epoxy resin.
The organosilicon modified epoxy resin prepared in the embodiment is cured at normal temperature by adopting an amine curing agent, and the main performance indexes of the organosilicon modified epoxy resin after 24 hours are shown in table 1.
TABLE 1
The above test results were referred to the following test standards.
Tensile strength assay, GB/6329-1986;
shear strength determination, GB/7124-1986;
hardness determination, GB/6739-;
water absorption determination method, at normal temperature, the condensate is soaked in water for 30 days, and the mass of the condensate is increased by percentage;
decomposition temperature measurement method, temperature at which the cured product starts to change after heating;
corrosion resistance test, the cured product is tested by immersion in a 20% (w%) sulfuric acid solution.
Claims (8)
1. A preparation method of organosilicon modified epoxy resin is characterized by comprising the following steps: it comprises the following steps:
step one, preparing organic silicon oligomer: according to the mass parts, 30-40 parts of alkoxy silane monomer and 5-10 parts of solvent A are added into a reactor provided with a heating, stirring and refluxing device; heating to 80 ℃ under a stirring state, beginning to dropwise add a mixed solution consisting of 2-5 parts of catalyst A and 20-30 parts of distilled water, controlling the dropwise adding time to be 1-1.5h, keeping the temperature to be 80-90 ℃ after the dropwise adding is finished, reacting for 2h, then distilling under reduced pressure for 0.5-1h, evaporating ethanol and part of solvent generated by the reaction, cooling to room temperature, and filtering to obtain the organic silicon oligomer with the ethoxy mass percent content of 5-10% and the solid mass percent content of more than 80%;
step two, preparing the organosilicon modified epoxy resin: according to the mass parts, 5-10 parts of solvent B, 1-3 parts of catalyst B, 10-15 parts of organic silicon oligomer prepared in the step one and 40-50 parts of bisphenol A epoxy resin are sequentially added into a reactor provided with a heating, stirring and refluxing device, nitrogen is introduced for protection, the temperature is raised to 80 ℃ under the stirring state for reaction for 1-1.5h, the temperature is raised to 120 ℃ for reaction for 3-4h, and then reduced pressure distillation is carried out for 0.5-1h, so as to prepare the organic silicon modified epoxy resin.
2. The method for preparing an organosilicon modified epoxy resin according to claim 1, wherein: in the first step, the alkoxy silane monomer is selected from the compounds with the following structural general formula:
Y(4-n)Si(OR)n;
wherein Y represents a phenyl group or a primary or secondary alkyl group having 1 to 4 carbon atoms, R represents an alkyl group having 1 to 3 carbon atoms, and n is an integer of 1 to 4.
3. The method for preparing an organosilicon-modified epoxy resin according to claim 1 or 2, wherein: the alkoxy silane monomer comprises at least one of dimethyl diethoxy silane, monomethyl triethoxy silane or diphenyl diethoxy silane.
4. The method for preparing an organosilicon modified epoxy resin according to claim 3, wherein: in the second step, the bisphenol A type epoxy resin is epoxy resin E-44 or epoxy resin E-51, and the epoxy value is 0.41-0.54mol/100 g.
5. The method for preparing an organosilicon modified epoxy resin according to claim 4, wherein: in the step one, the catalyst A is hydrochloric acid or phosphoric acid.
6. The method for preparing an organosilicon modified epoxy resin according to claim 5, wherein: and in the second step, the catalyst B is at least one of dibutyl tin dilaurate or butyl titanate.
7. The method for preparing an organosilicon modified epoxy resin according to claim 6, wherein: in the first step, the solvent methyl is at least one of xylene, butyl acetate or butanol.
8. The method for preparing an organosilicon modified epoxy resin according to claim 7, wherein: and in the second step, the solvent B is at least one of dimethylbenzene and butanol.
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CN112062968A (en) * | 2020-09-01 | 2020-12-11 | 邹华智 | Epoxy resin curing agent and preparation method thereof |
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