CN110172157A - A kind of modified organic silicone resin and its preparation method and application - Google Patents
A kind of modified organic silicone resin and its preparation method and application Download PDFInfo
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- CN110172157A CN110172157A CN201810865105.1A CN201810865105A CN110172157A CN 110172157 A CN110172157 A CN 110172157A CN 201810865105 A CN201810865105 A CN 201810865105A CN 110172157 A CN110172157 A CN 110172157A
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- silicone resin
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- organic silicone
- graphene oxide
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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
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/001—Macromolecular compounds containing organic and inorganic sequences, e.g. organic polymers grafted onto silica
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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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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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Abstract
The invention discloses a kind of modified organic silicone resins and its preparation method and application, and by being modified to obtain to organic siliconresin using Silane Grafted graphene oxide as reinforcing agent, the dosage of Silane Grafted graphene oxide is the 0.01-1wt.% of organic siliconresin.The reunion of graphene is both effectively prevented using organic siliconresin prepared by method of the invention, while significantly improving the corrosion resistance of organic siliconresin.
Description
Technical field
The invention belongs to organic siliconresin technical fields, and in particular to a kind of Silane Grafted graphene oxide modified organic silicon
Resin and its preparation method and application.
Background technique
Organic siliconresin (also referred to as polysiloxanes) is that a kind of alternately linked by silicon atom and oxygen atom forms skeleton, difference
Organic group again with silicon atom connection polymer general designation.The main chain of organic siliconresin is Si-O key, bond energy 452kJ/
Mol, therefore be not easy to be decomposed by ultraviolet light and ozone, so organosilicon has thermal stability more better than other high molecular materials
And radiation hardness and weather resistance, no matter chemical property or physical mechanical property, variation with temperature all very littles can be at one
It is used within the scope of very wide temperature, service life in a natural environment is up to decades.Since the main chain of organosilicon is very soft
Suitable, intermolecular force ratio hydrocarbon wants much weaker, and then, surface lower than the hydrocarbon viscosity of same molecular weight
Tension is weak, surface energy is small, film forming ability is strong, and has the physical characteristic of low surface tension and low-surface-energy.But it is organic at present
The corrosion resistance that silicone resin is applied in anticorrosive paint still has to be hoisted.
Graphene is the two-dimentional carbon nanomaterial with excellent physical and chemical performance newfound in recent years, big specific surface
Product, heat/chemical stability and excellent barrier property become the research hotspot of coating high-performance corrosion inhibitor.However
Dispersibility of the graphene in colloidal sol is excessively poor, and high specific surface area, strong Van der Waals force and pi-pi bond effect lead to graphene
Easily reunite, not only shielding action cannot be generated to corrosive medium, it is also possible to form vapor channel, hydrone is accelerated to apply
Diffusion rate in layer, reduces the mechanical performance and antiseptic property of coating.
Summary of the invention
Technical purpose of the invention is in view of the above deficiencies, to provide a kind of Silane Grafted graphene oxide modified organic silicon tree
Rouge and preparation method thereof both effectively prevents the reunion of graphene using organic siliconresin prepared by this method, while significantly mentioning
The high corrosion resistance of organic siliconresin.
A kind of modified organic silicone resin is to change using Silane Grafted graphene oxide as reinforcing agent to organic siliconresin
What property obtained, the dosage of Silane Grafted graphene oxide is the 0.01-1 wt. % of organic siliconresin.
Preferably, the Silane Grafted graphene oxide is that amido organosilicon oxygen alkane is passed through amidation process and epoxy
Ring-opening reaction obtains graphene oxide modification.
Preferably, the amido organosilicon oxygen alkane is to contain at least one free-NH2Organosiloxane compound
Object.
Preferably, the amido organosilicon oxygen alkane is selected from γ-aminopropyltrimethoxysilane, gamma-aminopropyl-triethoxy
Silane, N- (β-aminoethyl)-γ-aminopropyltrimethoxysilane, N- (β-aminoethyl)-gamma-aminopropyl-triethoxy-silane, 3-
Ureido-propyl trimethoxy silane, 3- ureidopropyltriethoxysilane, 4- amino -3,3- dimethylbutyl trimethoxy silane
Or the combination of one or more of diethylenetriamine base propyl trimethoxy silicane.
The preparation method of above-mentioned modified organic silicone resin, comprising the following steps:
Step 1, chlorosilane is hydrolyzed, obtains hydrolyzation material 1；
Step 2, acidic catalyst is added to hydrolyzation material 1 and adjusts pH to 3-6, obtain hydrolyzation material 2；
Step 3, under the conditions of 5-95 DEG C, Silane Grafted graphene oxide is added into hydrolyzation material 2, is hydrolyzed after mixing evenly
Material 3；
Step 4, basic catalyst is added to hydrolyzation material 3 and adjusts pH to 5-7, obtain hydrolyzation material 4；
Step 5, hydrolyzation material 4 is subjected to polycondensation reaction, obtains modified organic silicone resin.
Preferably, the acidic catalyst is selected from HCOOH, C2H5COOH、HCl、H2SO4、HNO3、H3PO4、HF、HBr、
H2SeO4、HClO4Or H2SO3One or more of combination.
Preferably, the basic catalyst is selected from NH3•H2O、NaHCO3Or NaCO3One or more of group
It closes.
Preferably, the chlorosilane is selected from methyl trichlorosilane, diformazan base trichlorosilane, benzyl trichlorosilane, two
The mixture of one or more of benzyl dichlorosilane or trim,ethylchlorosilane.
Above-mentioned modified organic silicone resin is preparing the application in metal anti-corrosive paint.
The present invention by introducing specific Silane Grafted graphene oxide in organic siliconresin as reinforcing agent, thus
Organic siliconresin corrosion resistance is modified, the modified organic siliconresin of Silane Grafted graphene oxide is obtained, and it is existing
Organic siliconresin in technology is compared, and is had the following beneficial effects:
(1) graphene oxide that the reinforcing agent selects amino silicone modified makes surface of graphene oxide be grafted upper alkoxy, makes
Hydrolysis-condensation reaction occurs with organosilicon hydrolyzation material in it jointly, is finally dispersed stably in graphene in organic siliconresin, resistance
The reunion of graphene is stopped.
(2) graphene synergist is stably dispersed in silicone resin system by dehydrating condensation chemical action, to mention
The high corrosion resistance of silicone resin coating.
It is demonstrated experimentally that compared with no added organic siliconresin, using the Silane Grafted graphene oxide of this method preparation
Modified organic siliconresin has better anticorrosion effect.
Detailed description of the invention
Fig. 1 is that organic siliconresin obtained by embodiment and comparative example is added after pigments and fillers coating spray proof 60 days
Salt spray test result.
Specific embodiment
Present invention is further described in detail with reference to embodiments, it should be pointed out that embodiment described below purport
It is being convenient for the understanding of the present invention, and is not playing any restriction effect to it.
Comparative example 1
This comparative example uses prior art preparation organic siliconresin, the specific steps are as follows:
(1) 300g methyl trichlorosilane and 260g dimethyldichlorosilane are added drop-wise to 1100g toluene at 20~30 DEG C
And in 2500g water, after being added dropwise, it is stirred for 30 minutes, obtains organosilicon hydrolyzation material 1-1；
(2) hydrolyzation material 1-1 is washed to pH close to 7, obtains hydrolyzation material 2-1；
(3) after hydrolyzation material 2-1 being heated to 60 DEG C, toluene is collected in distillation at 200mmHg, is reached to system temperature
120 DEG C, stop heating, cooling obtains organic siliconresin OSR-1.
Comparative example 2
This comparative example uses prior art preparation organic siliconresin, the specific steps are as follows:
(1) 422g phenyl trichlorosilane and 506g diphenyl dichlorosilane are added drop-wise to 1100 toluene at 20~30 DEG C
In 2500g water, after being added dropwise, it is stirred for 30 minutes, obtains organosilicon hydrolyzation material 1-2；
(2) hydrolyzation material 1-2 is washed to pH close to 5, obtains hydrolyzation material 2-2；
(3) after hydrolyzation material 2-2 being heated to 50 DEG C, toluene is collected in distillation at 200mmHg, reaches 120 to system temperature
DEG C, stop heating, cooling obtains organic siliconresin OSR-2.
Comparative example 3
This comparative example uses prior art preparation organic siliconresin, the specific steps are as follows:
(1) by 149g methyl trichlorosilane, 129g dimethyl dichloro silicon, 211g phenyl trichlorosilane and 176g diphenyl
Dichlorosilane is added drop-wise in 1100g toluene and 2500g water at 20~30 DEG C, after being added dropwise, is stirred for 30 minutes,
Obtain organosilicon hydrolyzation material 1-3；
(2) hydrolyzation material 1-3 is washed to pH close to 6, obtains hydrolyzation material 2-3；
(3) after hydrolyzation material 2-3 being heated to 60 DEG C, toluene is collected in distillation at 200mmHg, reaches 120 to system temperature
DEG C, stop heating, cooling obtains organic siliconresin OSR-3.
Embodiment 1
The present embodiment uses gamma-aminopropyl-triethoxy-silane grafted graphene oxide modified organic silicone resin, and specific steps are such as
Under:
(1) 1g graphene oxide, 0.5g dicyclohexylcarbodiimide, 0.5g 4-dimethylaminopyridine ultrasonic disperse are existed
70 DEG C of constant temperature stir for 24 hours after 1 hour in 100mL aminopropyltriethoxywerene werene.Mixed liquor centrifugation simultaneously will be centrifuged product nothing
Water-ethanol cleaning obtains the modified graphene oxide of aminopropyltriethoxywerene werene after vacuum drying.
(2) 300g methyl trichlorosilane and 260g and dimethyldichlorosilane are added drop-wise at 20~30 DEG C
In 1100g toluene and 2500g water, after being added dropwise, it is stirred for 30 minutes, obtains organosilicon hydrolyzation material 1-4；
(3) washing hydrolyzation material 1-4 to pH is 3, obtains hydrolyzation material 2-4；
(4) it takes 1000g hydrolyzation material 2-4 to be heated to 60 DEG C, 5g Silane Grafted graphene oxide is added wherein, stir 10 points
Clock obtains hydrolyzation material 3-4；
(5) hydrolyzation material 3-4 is washed to pH close to 7, obtains hydrolyzation material 4-4；
(6) after hydrolyzation material 4-4 being heated to 60 DEG C, toluene is collected in distillation at 200mmHg, reaches 120 DEG C to system temperature,
Stop heating, cooling obtains organic functional modified organic siliconresin OSR-4.
Embodiment 2
The present embodiment uses gamma-aminopropyl-triethoxy-silane grafted graphene oxide modified organic silicone resin, and specific steps are such as
Under:
(1) 1g graphene oxide, 0.5g dicyclohexylcarbodiimide, 0.5g 4-dimethylaminopyridine ultrasonic disperse are existed
70 DEG C of constant temperature stir for 24 hours after 1 hour in 100mL aminopropyltriethoxywerene werene.Mixed liquor centrifugation simultaneously will be centrifuged product nothing
Water-ethanol cleaning obtains the modified graphene oxide of aminopropyltriethoxywerene werene after vacuum drying.
(2) 422g phenyl trichlorosilane and 506g diphenyl dichlorosilane are added drop-wise to 1100 at 20~30 DEG C
In toluene 2500g water, after being added dropwise, it is stirred for 30 minutes, obtains organosilicon hydrolyzation material 1-5；
(3) hydrolyzation material 1-5 is washed to pH close to 5, obtains hydrolyzation material 2-5；
(4) it takes 1000g hydrolyzation material 2-5 to be heated to 60 DEG C, 5g Silane Grafted graphene oxide is added wherein, stir 10 points
Clock obtains hydrolyzation material 3-5；
(5) hydrolyzation material 3-5 is washed to pH close to 7, obtains hydrolyzation material 4-5；
(6) after hydrolyzation material 4-5 being heated to 60 DEG C, toluene is collected in distillation at 200mmHg, reaches 120 DEG C to system temperature,
Stop heating, cooling obtains organic functional modified organic siliconresin OSR-5.
Embodiment 3
The present embodiment uses gamma-aminopropyl-triethoxy-silane grafted graphene oxide modified organic silicone resin, and specific steps are such as
Under:
(1) 1g graphene oxide, 0.5g dicyclohexylcarbodiimide, 0.5g 4-dimethylaminopyridine ultrasonic disperse are existed
70 DEG C of constant temperature stir for 24 hours after 1 hour in the aminopropyltriethoxywerene werene of 100mL.Mixed liquor centrifugation simultaneously uses centrifugation product
Washes of absolute alcohol obtains the modified graphene oxide of aminopropyltriethoxywerene werene after vacuum drying.
(2) by 149g methyl trichlorosilane, 129g dimethyl dichloro silicon, 211g phenyl trichlorosilane and 176g bis-
Diphenyl dichlorosilane is added drop-wise in 1100g toluene and 2500g water at 20~30 DEG C, after being added dropwise, is stirred for 30 points
Clock obtains organosilicon hydrolyzation material 1-6；
(3) hydrolyzation material 1-6 is washed to pH close to 6, obtains hydrolyzation material 2-6；
(4) it takes 1000g hydrolyzation material 2-6 to be heated to 60 DEG C, 5g Silane Grafted graphene oxide is added wherein, stir 10 points
Clock obtains hydrolyzation material 3-6；
(5) hydrolyzation material 3-6 is washed to pH close to 7, obtains hydrolyzation material 4-5；
(6) after hydrolyzation material 4-6 being heated to 60 DEG C, toluene is collected in distillation at 200mmHg, reaches 120 DEG C to system temperature,
Stop heating, cooling obtains organic functional modified organic siliconresin OSR-6.
The organic siliconresin prepared to above-mentioned comparative example 1,2,3 and embodiment 1,2,3 is coated in Q235 stainless steel
Surface carries out the test of the corrosive natures such as salt fog, polarization curve, electrochemical impedance spectroscopy.If Fig. 1 is that embodiment and comparative example have
60 days salt spray test results of coating spray proof after pigments and fillers are added in machine silicone resin.Test result shows to aoxidize by Silane Grafted
The excellent anti-corrosion performance of the modified organosilicon tree (embodiment 1,2,3) of graphene is in the organic siliconresin of prior art preparation
(comparative example 1,2,3).
Claims (9)
1. a kind of modified organic silicone resin, it is characterised in that: by using Silane Grafted graphene oxide as reinforcing agent to organic
What silicone resin was modified, the dosage of Silane Grafted graphene oxide is the 0.01-1wt. % of organic siliconresin.
2. modified organic silicone resin according to claim 1, it is characterised in that: the Silane Grafted graphene oxide be by
Amido organosilicon oxygen alkane obtains graphene oxide modification by amidation process and epoxy ring opening reaction.
3. modified organic silicone resin according to claim 2, it is characterised in that: the amido organosilicon oxygen alkane is at least to wrap
Containing a free-NH2Organosilicone compounds.
4. modified organic silicone resin according to claim 3, it is characterised in that: the amido organosilicon oxygen alkane is selected from γ-
Aminopropyl trimethoxysilane, gamma-aminopropyl-triethoxy-silane, N- (β-aminoethyl)-γ-aminopropyltrimethoxysilane,
N- (β-aminoethyl)-gamma-aminopropyl-triethoxy-silane, 3- ureido-propyl trimethoxy silane, 3- ureido-propyl triethoxy
One of silane, 4- amino -3,3- dimethylbutyl trimethoxy silane or diethylenetriamine base propyl trimethoxy silicane
Or two or more combination.
5. the preparation method of modified organic silicone resin described in claim 1, it is characterised in that: the following steps are included:
Step 1, chlorosilane is hydrolyzed, obtains hydrolyzation material 1；
Step 2, acidic catalyst is added to hydrolyzation material 1 and adjusts pH to 3-6, obtain hydrolyzation material 2；
Step 3, under the conditions of 5-95 DEG C, Silane Grafted graphene oxide is added into hydrolyzation material 2, is hydrolyzed after mixing evenly
Material 3；
Step 4, basic catalyst is added to hydrolyzation material 3 and adjusts pH to 5-7, obtain hydrolyzation material 4；
Step 5, hydrolyzation material 4 is subjected to polycondensation reaction, obtains modified organic silicone resin.
6. the preparation method of modified organic silicone resin according to claim 5, it is characterised in that: the acidic catalyst choosing
From HCOOH, C2H5COOH、HCl、H2SO4、HNO3、H3PO4、HF、HBr、H2SeO4、HClO4Or H2SO3One or both of with
On combination.
7. the preparation method of modified organic silicone resin according to claim 5, it is characterised in that: the basic catalyst choosing
From NH3•H2O、NaHCO3Or NaCO3One or more of combination.
8. the preparation method of modified organic silicone resin according to claim 5, it is characterised in that: the chlorosilane is selected from first
One in base trichlorosilane, diformazan base trichlorosilane, benzyl trichlorosilane, benzhydryl dichlorosilane or trim,ethylchlorosilane
Kind or several mixtures.
9. modified organic silicone resin described in claim 1 is preparing the application in metal anti-corrosive paint.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113444420A (en) * | 2021-05-14 | 2021-09-28 | 高维川 | Epoxy resin-graphene/graphene oxide composite coating and preparation method thereof |
| CN114292590A (en) * | 2022-01-11 | 2022-04-08 | 北京裕金科技有限公司 | Graphene oxide modified organic silicon coating and preparation method and application thereof |
| CN114292561A (en) * | 2021-12-06 | 2022-04-08 | 广东美涂士建材股份有限公司 | Organic silicon graphene industrial coating and preparation method thereof |
| CN114410220A (en) * | 2022-01-11 | 2022-04-29 | 北京裕金科技有限公司 | Application of graphene modified organic silicon resin coating as material for protecting ancient architecture colored drawing cultural relics |
| CN115863745A (en) * | 2022-03-08 | 2023-03-28 | 广西柳工机械股份有限公司 | Polymer/graphene composite solid electrolyte membrane and preparation method thereof |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113444420A (en) * | 2021-05-14 | 2021-09-28 | 高维川 | Epoxy resin-graphene/graphene oxide composite coating and preparation method thereof |
| CN114292561A (en) * | 2021-12-06 | 2022-04-08 | 广东美涂士建材股份有限公司 | Organic silicon graphene industrial coating and preparation method thereof |
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| CN114410220A (en) * | 2022-01-11 | 2022-04-29 | 北京裕金科技有限公司 | Application of graphene modified organic silicon resin coating as material for protecting ancient architecture colored drawing cultural relics |
| CN115863745A (en) * | 2022-03-08 | 2023-03-28 | 广西柳工机械股份有限公司 | Polymer/graphene composite solid electrolyte membrane and preparation method thereof |
| CN115863745B (en) * | 2022-03-08 | 2023-11-14 | 广西柳工机械股份有限公司 | Polymer/graphene composite solid electrolyte membrane and preparation method thereof |
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