CN111116925A - Organic silicon modified epoxy composite resin with fluorescent characteristic - Google Patents
Organic silicon modified epoxy composite resin with fluorescent characteristic Download PDFInfo
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- CN111116925A CN111116925A CN201911169885.7A CN201911169885A CN111116925A CN 111116925 A CN111116925 A CN 111116925A CN 201911169885 A CN201911169885 A CN 201911169885A CN 111116925 A CN111116925 A CN 111116925A
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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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
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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
- 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
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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
- C09D183/10—Block or graft copolymers containing polysiloxane sequences
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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
- C09D187/00—Coating compositions based on unspecified macromolecular compounds, obtained otherwise than by polymerisation reactions only involving unsaturated carbon-to-carbon bonds
- C09D187/005—Block or graft polymers not provided for in groups C09D101/00 - C09D185/04
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/18—Fireproof paints including high temperature resistant paints
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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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/22—Luminous paints
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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
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- Polymers & Plastics (AREA)
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Abstract
The invention discloses an organic silicon modified epoxy composite resin with a fluorescent characteristic, which is prepared from the following raw materials in percentage by mass: 10-24 wt% of amino silicone oil; 5-8 wt% of tetra-p-carboxyl tetraphenylethylene; 75-89 wt% of bisphenol A type epoxy resin. According to the invention, the fluorescent molecules with aggregation-induced emission effect are connected to the composite resin through chemical bonds, and due to the combined action of polymer chain wrapping and chemical bond connection, the intramolecular rotation of the fluorescent molecules is inhibited, so that the fluorescent emission behavior of the resin is realized.
Description
Technical Field
The invention relates to the field of anticorrosive resin, in particular to organic silicon modified epoxy composite resin with a fluorescent characteristic.
Background
In the field of corrosion protection of material surface layers, it is known to use anticorrosive coatings of different compositions to achieve corrosion protection of material surface layers. For material anticorrosion engineering, the anticorrosive coating plays an important role all the time due to the advantages of simple and convenient construction process, obvious effect, low cost, outstanding performance, long service life and the like. In the process of researching and improving the corrosion resistance of the anticorrosive paint, the inventor finds that the anticorrosive paint in the prior art has at least the following problems:
the traditional anticorrosive paint has an important role as epoxy resin of polymer resin, and a cured paint film of the traditional anticorrosive paint has the advantages of strong adhesion to a substrate, small curing shrinkage, high mechanical property, good chemical stability and the like, but has the defects of low impact resistance, poor stress cracking resistance, poor heat resistance and the like in the use process after curing.
In order to solve the above problems, it is necessary to modify the epoxy resin, optimize the mechanical properties thereof, and realize the functional application thereof.
Disclosure of Invention
Aiming at the defects in the prior art, the invention mainly aims to provide the organic silicon modified epoxy composite resin with the fluorescence characteristic, wherein fluorescent molecules with aggregation-induced emission effect are connected to the composite resin through chemical bonds, and due to the combined action of polymer chain wrapping and chemical bond connection, the intramolecular rotation of the fluorescent molecules is inhibited, so that the fluorescent emission behavior of the resin is realized.
The invention also aims to provide the organic silicon modified epoxy composite resin with the fluorescent characteristic, which utilizes organic silicon oil with the fluorescent characteristic to chemically modify the epoxy resin, fully utilizes the advantages of low surface energy, good thermal stability, oxidation resistance, high dielectric strength, good low-temperature flexibility and the like of organic silicon, and improves the mechanical property of the epoxy resin.
In order to achieve the above objects and other advantages according to the present invention, there is provided a silicone-modified epoxy composite resin having fluorescent characteristics, which is made of the following raw materials in mass percent:
10-24 wt% of amino silicone oil;
5-8 wt% of tetra-p-carboxyl tetraphenylethylene;
75-89 wt% of bisphenol A type epoxy resin;
the organic silicon modified epoxy composite resin is prepared by the following steps:
step 1, mixing amino silicone oil and tetra-p-carboxyl tetraphenyl ethylene according to the designed parts by weight to prepare a mixed solution, adding a dibutyltin dilaurate catalyst into the mixed solution, heating to 60-90 ℃, stirring and heating for reaction for 4-24 hours to obtain an intermediate of modified amino silicone oil;
and 2, mixing the modified amino silicone oil intermediate prepared in the step 1 with a designed amount of bisphenol A epoxy resin, heating to 150-200 ℃, stirring, heating, reacting for 12-24 hours, and cooling to obtain the organic silicon modified epoxy composite resin with the fluorescent characteristic.
Optionally, the amount of the dibutyltin dilaurate catalyst added is 0.01 to 0.1 wt% based on the total mass of the mixed solution prepared in the step 1.
Optionally, the amino silicone oil has an ammonia value of 0.6 and a viscosity range of 300-1000 (25 ℃, centipoise).
Optionally, the epoxy value range of the bisphenol A epoxy resin is 0.12mol/100 g-0.51 mol/100 g.
One of the above technical solutions has the following advantages or beneficial effects: because the fluorescent molecules with aggregation-induced emission effect are connected to the composite resin through chemical bonds, the molecular rotation of the fluorescent molecules is inhibited due to the combined action of polymer chain wrapping and the chemical bonds, and the fluorescent emission behavior of the resin is realized.
Another technical scheme in the above technical scheme has the following advantages or beneficial effects: because the epoxy resin is chemically modified by using the organic silicon oil with the fluorescent characteristic, the organic silicon has the advantages of low surface energy, good thermal stability, oxidation resistance, high dielectric strength, good low-temperature flexibility and the like, and the mechanical property of the epoxy resin is improved.
Drawings
Fig. 1 is a fluorescent luminous picture of an organosilicon modified epoxy composite resin with fluorescent property under an ultraviolet lamp, which is prepared according to a first embodiment of the invention;
fig. 2 shows a cured coating of a silicone-modified epoxy composite resin having fluorescent properties prepared according to example one of the present invention (curing agent: polyamide 650, silicone-modified epoxy composite resin: polyamide 650 curing agent ═ 1:1(w/w), solvent: xylene, resin curing agent solid content: 60%).
Detailed Description
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Example one
An organosilicon modified epoxy composite resin with fluorescence characteristics is prepared from the following raw materials in percentage by mass:
10 wt% of amino silicone oil;
tetra-p-carboxytetraphenylethylene, 1 wt%;
89 wt% of bisphenol A type epoxy resin;
the organic silicon modified epoxy composite resin is prepared by the following steps:
step 1, mixing amino silicone oil and tetra-p-carboxyl tetraphenyl ethylene according to the designed parts by weight to prepare a mixed solution, adding a dibutyltin dilaurate catalyst into the mixed solution, heating to 60 ℃, stirring and heating for reaction for 24 hours to obtain an intermediate of modified amino silicone oil;
and 2, mixing the modified amino silicone oil intermediate prepared in the step 1 with a designed amount of bisphenol A epoxy resin, heating to 200 ℃, stirring, heating, reacting for 12 hours, and cooling to obtain the organic silicon modified epoxy composite resin with the fluorescent characteristic.
Further, the amount of dibutyltin dilaurate catalyst added was 0.05 wt% based on the total mass of the mixed solution prepared in step 1.
Further, the amino silicone oil has an ammonia value of 0.6 and a viscosity in the range of 1000(25 ℃, cps).
Further, the epoxy value of the bisphenol A type epoxy resin is in the range of 0.51mol/100 g.
Example two
An organosilicon modified epoxy composite resin with fluorescence characteristics is prepared from the following raw materials in percentage by mass:
24 wt% of amino silicone oil;
tetra-p-carboxytetraphenylethylene, 0.1 wt%;
bisphenol A type epoxy resin, 75.9 wt%;
the organic silicon modified epoxy composite resin is prepared by the following steps:
step 1, mixing amino silicone oil and tetra-p-carboxyl tetraphenyl ethylene according to the designed parts by weight to prepare a mixed solution, adding a dibutyltin dilaurate catalyst into the mixed solution, heating to 75 ℃, stirring and heating for reaction for 16 hours to obtain an intermediate of modified amino silicone oil;
and 2, mixing the modified amino silicone oil intermediate prepared in the step 1 with a designed amount of bisphenol A epoxy resin, heating to 180 ℃, stirring, heating, reacting for 18 hours, and cooling to obtain the organic silicon modified epoxy composite resin with the fluorescent characteristic.
Further, the amount of dibutyltin dilaurate catalyst added was 0.01 wt% based on the total mass of the mixed solution prepared in step 1.
Further, the amino silicone oil had an ammonia value of 0.6 and a viscosity in the range of 500(25 ℃, cps).
Further, the epoxy value of the bisphenol A type epoxy resin is in the range of 0.44mol/100 g.
EXAMPLE III
An organosilicon modified epoxy composite resin with fluorescence characteristics is prepared from the following raw materials in percentage by mass:
23 wt% of amino silicone oil;
tetra-p-carboxytetraphenylethylene, 2 wt%;
bisphenol A type epoxy resin, 75 wt%;
the organic silicon modified epoxy composite resin is prepared by the following steps:
step 1, mixing amino silicone oil and tetra-p-carboxyl tetraphenyl ethylene according to the designed parts by weight to prepare a mixed solution, adding a dibutyltin dilaurate catalyst into the mixed solution, heating to 90 ℃, stirring and heating for reaction for 4 hours to obtain an intermediate of modified amino silicone oil;
and 2, mixing the modified amino silicone oil intermediate prepared in the step 1 with a designed amount of bisphenol A epoxy resin, heating to 150 ℃, stirring, heating, reacting for 24 hours, and cooling to obtain the organic silicon modified epoxy composite resin with the fluorescent characteristic.
Further, the amount of dibutyltin dilaurate catalyst added was 0.1 wt% based on the total mass of the mixed solution prepared in step 1.
Further, the amino silicone oil had an ammonia value of 0.6 and a viscosity in the range of 300(25 ℃, cps).
Further, the epoxy value of the bisphenol A type epoxy resin is in the range of 0.12mol/100 g.
Polyamide 650 resin is used as a curing agent, and the organic silicon modified epoxy composite resin with the fluorescent characteristic and the curing agent are mixed according to the weight ratio of 1:1, mixing, dissolving in a xylene solvent, adjusting the solid content to 60%, coating the prepared coating on the surface of a metal substrate in a brushing mode, and curing at room temperature to obtain the anticorrosive coating with the fluorescent characteristic. Table one shows the properties of the paint films prepared for each sample.
TABLE I cured coating performance based on organosilicon modified epoxy composite resin
Referring to table one and the illustrations in conjunction with fig. 1 and 2, it can be concluded that: compared with the first, second and third examples, the prepared coating has stronger fluorescence intensity due to copolymerization modification of amino silicone oil with fluorescence characteristic; along with the increase of the content of the amino silicone oil, the flexibility of a paint film is enhanced, the contact angle of a paint surface is increased, the water resistance of the coating is improved, but the hardness is reduced; in addition, the composite coating exhibits good results in terms of both heat resistance and corrosion resistance.
While embodiments of the invention have been disclosed above, it is not limited to the applications listed in the description and the embodiments, which are fully applicable in all kinds of fields of application of the invention, and further modifications may readily be effected by those skilled in the art, whereby the invention is not limited to the details given, without departing from the general concept defined by the claims and the scope of equivalents.
Claims (4)
1. The organic silicon modified epoxy composite resin with the fluorescent characteristic is characterized by being prepared from the following raw materials in percentage by mass:
10-24 wt% of amino silicone oil;
5-8 wt% of tetra-p-carboxyl tetraphenylethylene;
75-89 wt% of bisphenol A type epoxy resin;
the organic silicon modified epoxy composite resin is prepared by the following steps:
step 1, mixing amino silicone oil and tetra-p-carboxyl tetraphenyl ethylene according to the designed parts by weight to prepare a mixed solution, adding a dibutyltin dilaurate catalyst into the mixed solution, heating to 60-90 ℃, stirring and heating for reaction for 4-24 hours to obtain an intermediate of modified amino silicone oil;
and 2, mixing the modified amino silicone oil intermediate prepared in the step 1 with a designed amount of bisphenol A epoxy resin, heating to 150-200 ℃, stirring, heating, reacting for 12-24 hours, and cooling to obtain the organic silicon modified epoxy composite resin with the fluorescent characteristic.
2. The organic silicon modified epoxy composite resin with fluorescent characteristic of claim 1, wherein the amount of dibutyltin dilaurate catalyst added is 0.01 to 0.1 wt% based on the total mass of the mixed solution prepared in step 1.
3. The organic silicon modified epoxy composite resin with fluorescent characteristic of claim 1, wherein the amino silicone oil has an ammonia value of 0.6 and a viscosity range of 300 to 1000(25 ℃, centipoise).
4. The silicone-modified epoxy composite resin having fluorescent properties according to claim 1, wherein the epoxy value of the bisphenol a type epoxy resin is in the range of 0.12mol/100g to 0.51mol/100 g.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN112482040A (en) * | 2020-11-19 | 2021-03-12 | 江苏科技大学 | Super-hydrophobic fiber cloth with fluorescent property and preparation method thereof |
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US20110251305A1 (en) * | 2010-04-07 | 2011-10-13 | Manabu Ueno | Epoxy composition for encapsulating an optical semiconductor element |
CN106008920A (en) * | 2016-06-26 | 2016-10-12 | 苏州吉人高新材料股份有限公司 | Modified epoxy resin with fluorescent characteristic and preparation method thereof |
CN106349460A (en) * | 2016-09-05 | 2017-01-25 | 华南理工大学 | High-temperature-resistant organic silicon-modified epoxy resin and method for preparing same |
CN106751516A (en) * | 2016-12-16 | 2017-05-31 | 武汉大学 | A kind of toughness reinforcing, heat-resisting modified epoxy and preparation method thereof |
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2019
- 2019-11-26 CN CN201911169885.7A patent/CN111116925A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US20110251305A1 (en) * | 2010-04-07 | 2011-10-13 | Manabu Ueno | Epoxy composition for encapsulating an optical semiconductor element |
CN106008920A (en) * | 2016-06-26 | 2016-10-12 | 苏州吉人高新材料股份有限公司 | Modified epoxy resin with fluorescent characteristic and preparation method thereof |
CN106349460A (en) * | 2016-09-05 | 2017-01-25 | 华南理工大学 | High-temperature-resistant organic silicon-modified epoxy resin and method for preparing same |
CN106751516A (en) * | 2016-12-16 | 2017-05-31 | 武汉大学 | A kind of toughness reinforcing, heat-resisting modified epoxy and preparation method thereof |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112482040A (en) * | 2020-11-19 | 2021-03-12 | 江苏科技大学 | Super-hydrophobic fiber cloth with fluorescent property and preparation method thereof |
CN112482040B (en) * | 2020-11-19 | 2022-03-29 | 江苏科技大学 | Super-hydrophobic fiber cloth with fluorescent property and preparation method thereof |
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