CN101864239A - Hyperbranched epoxy resin/polypyrrole composite anticorrosive paint and preparation method thereof - Google Patents
Hyperbranched epoxy resin/polypyrrole composite anticorrosive paint and preparation method thereof Download PDFInfo
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- CN101864239A CN101864239A CN 201010191318 CN201010191318A CN101864239A CN 101864239 A CN101864239 A CN 101864239A CN 201010191318 CN201010191318 CN 201010191318 CN 201010191318 A CN201010191318 A CN 201010191318A CN 101864239 A CN101864239 A CN 101864239A
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Abstract
The invention discloses a hyperbranched epoxy resin/polypyrrole composite anticorrosive paint and a preparation method thereof. The raw materials of the hyperbranched epoxy resin/polypyrrole composite anticorrosive paint comprise a component A and a component B, wherein the component A comprises 50-80 wt% of hyperbranched epoxy resin, 3-50 wt% of pyrrole and 0-20 wt% of diluent, the component B comprises 20-80 wt% of FeCl3, 10-70 wt% of curing agent and 1-10 wt% of diluent, and the weight ratio of the component A and the component B is (1-3):1. The hyperbranched epoxy resin/polypyrrole composite anticorrosive paint is prepared by simply mixing the component A and the component B according to the proportion and curing at 80 DEG C when in use. The anticorrosive paint prepared in the invention has excellent anticorrosive performance as well as physical and mechanical properties and is environment-friendly.
Description
Technical field
The present invention relates to a kind of protective system.Specifically, relate to a kind of hyperbranched epoxy resin/polypyrrole composite anticorrosive paint.
Background technology
The rust corrosion of metal products has caused resource, the waste of the energy and loss economically, sometimes even jeopardize personnel safety.Anti-corrosion of metal is important research direction of material industry always.General at present employing corrosion protection coating reaches the purpose that prevents or slow down metallic corrosion.And protective system major part commonly used at present all contains a large amount of organic solvents, must cause bigger harm to environment in coating procedure.On the other hand, existing protective system, especially boats and ships heavy-duty coating main function additive is heavy metallic salts such as inorganic, organic zinc or chromic salts, the former relies on the mass consumption metallic zinc to reach the rot-resistant purpose, so not only be subjected to the resource restriction of zinc, also ocean environment caused severe contamination, and heavy metallic salts such as chromic salts, not only harmful to environment, also might carcinogenesis be arranged to the people.Therefore, seeking novel free of contamination protective system has been an inexorable trend.
Conductive polymers is as the anti-corrosion function composition, with its good corrosion prevention performance, satisfactory stability and little to sticking power, the toxicity of metallic matrix, being considered to heavy metallic salts such as alternative inorganic, organic zinc or chromic salts gradually and being used in the protective system, is an important development direction of environment-friendly and green protective system additive.Be used for all conductive polymerss of rot-resistant, polypyrrole, Polythiophene, polyaniline are that research is maximum, the best several conductive polymerss of performance.The general employing aggregates into its polymer form with pyrroles, thiophene, aniline monomer earlier, adds traditional filmogen (as Resins, epoxy, urethane or polyacrylic resin etc.) again to and forms composite anti-corrosive paint film system.Conductive polymers is a solid, and whole system will be used a large amount of organic solvents inevitably, and this runs counter to the requirement of environmental protection coating material.
Bisphenol A type epoxy resin is low because of its bonding strength height, cure shrinkage, solidifies back physical strength height, medium-resistance is good, therefore, is the protective system resin kind of widespread use.But it is high viscosity liquid or solid-state, need add a large amount of organic solvents during use, and fragility is big after solidifying, and has limited its range of application.
Summary of the invention
Purpose of the present invention overcomes the deficiencies in the prior art and shortcoming exactly, and a kind of rare machine solvent, environmentally friendly and antiseptic property, composite anticorrosion coating system that physical and mechanical properties is good and preparation method thereof are provided.
A kind of hyperbranched epoxy resin/polypyrrole composite anticorrosive paint of the present invention is a two-pack, and by weight percentage, raw material comprises following material:
The A component:
Resins, epoxy: 50wt%～80wt%
Pyrroles: 3wt%～50wt%
Thinner: 0～20wt%
The B component:
FeCl
3： 20wt％～80wt％
Solidifying agent: 10wt%～70wt%
Thinner: 1wt%～10wt%
A component and B components by weight (1～3): 1.
Wherein: described Resins, epoxy is hyperbranched epoxy resin, structural formula as structural formula 1 or/and shown in 2.
Described thinner is alcohol or ketone compound; Described solidifying agent is NX-2041, and its reactive hydrogen equivalent is 82.
Described hyperbranched epoxy resin is the hyperbranched epoxy resin that is generated by dihydroxyphenyl propane, Resorcinol, Resorcinol, Bisphenol F, Hydrogenated Bisphenol A or bisphenol S and trihydroxymethylpropanyltri diglycidyl ether.
Described thinner is ethanol, Virahol, propyl carbinol, butanone or acetone.
During use at 80 ℃ of curing hyperbranched epoxy resin/polypyrrole composite anticorrosive paints.
Structural formula 1
Structural formula 2
In the said structure formula
The preparation method of above-mentioned hyperbranched epoxy resin/polypyrrole composite anticorrosive paint may further comprise the steps:
The preparation of I .A component:
(1) contracting above-mentioned bisphenol compound, Tetrabutyl amonium bromide, trimethylolpropane tris with mol ratio is 1: 0.03-0.08: 1.3-1.5 and DMF add and have reflux condensing tube, thermometer, stirring arm, N
2In the reactor of inlet, reacting by heating is after 24 hours in the nitrogen atmosphere, reaction system is cooled off, sink to then in a large amount of deionized waters, throw out acetone diluted then, anhydrous magnesium sulfate drying spends the night, and filter and remove sal epsom, and then deposition and purification obtains light yellow transparent liquid shape hyperbranched epoxy resin in ether;
Above-mentioned bisphenol compound is dihydroxyphenyl propane, Resorcinol, Resorcinol, Bisphenol F, Hydrogenated Bisphenol A or bisphenol S.
(2) promptly get the said A component of the present invention after will mixing by aforementioned weight percent by hyperbranched epoxy resin, thinner, the pyrroles that step (1) makes.
The preparation of II .B component
By aforementioned weight percent, with FeCl
3With a spot of thinner dissolving, the adding epoxy hardener mixes and promptly gets the said B component of the present invention.
III, with A component and B component by weight (1～3): 1 mixes, filters.
During use the gained coating compound is coated in through the metallic surface of oil removing, processing of rust removing, gauge control gets final product 80 ℃ of curing about 100 μ m.
The metal sheet that the said protective system of the present invention is applied carries out the physical and mechanical properties test and in 5wt%NaOH, 5wt%HCl, the experiment of 3.5wt%NaCl solution soaking, finds to have good physical and mechanical properties, medium-resistance.In the NaCl of 3.5wt% solution,, find that the metallic corrosion current potential increases substantially, and illustrates and has slowed down corrosive medium to corrosion of metal with the electrochemical etching method test.
The protective system that the present invention makes has excellent antiseptic property and physical and mechanical properties, and environmentally friendly.
Embodiment
The present invention is further illustrated by the following examples, and its purpose only is better to understand content of the present invention.Therefore, the cited case does not limit protection scope of the present invention.
Embodiment 1
The preparation of I .A component:
(1) Resorcinol, Tetrabutyl amonium bromide, trimethylolpropane tris being contracted with mol ratio is that 1: 0.05: 1.4 and DMF add and have reflux condensing tube, thermometer, stirring arm, N
2In the 1000mL four-hole bottle of inlet, reacting by heating is after 24 hours in the nitrogen atmosphere, with the reaction system cooling, sink in a large amount of deionized waters the throw out acetone diluted then, anhydrous magnesium sulfate drying spends the night, sal epsom is removed in filtration, and then deposition and purification obtains light yellow transparent liquid shape hyperbranched epoxy resin, weight-average molecular weight 3600 in ether, viscosity 4.5PaS
1H NMR (DMSO): δ (ppm)=0.765 (CH
3), 1.28 (CH
2), 2.512 (CH
2, epoxy group(ing)), 2.625 (OCH
2, epoxy group(ing)), 3.000 (OCH, epoxy group(ing)), 3.262-3.899 (OCH
2, CH (OH)), 4.960,5.029 (OH), 6.631-7.068 (CH, phenyl ring).IR (KBr) (cm
-1): 3500cm
-1(s, OH), 2945-2870cm
-1(s, CH), 1633-1515cm
-1(s, phenyl ring), 1248-1184cm
-1, 1075-1010cm
-1(s, C-O-C), 908cm
-1(w, epoxy group(ing)).
(2) hyperbranched epoxy resin that will make by step (1), acetone, pyrroles by content be respectively 70wt%, 20wt%, 10wt% promptly gets the said A component of the present invention after mixing.
The preparation of II .B component
With FeCl
3With the butanone dissolving, add epoxy hardener NX-2041 (the reactive hydrogen equivalent is 82) and mix FeCl
3, butanone and epoxy hardener NX-2041 weight percent be respectively 25wt%, 5wt%, 70wt% and promptly get the said B component of the present invention.
A component and B compositions in weight percentage are mixed, filter at 2: 1, then the gained mixture is coated in metallic surface through oil removing, processing of rust removing, gauge control is about 100 μ m, after room temperature after 80 ℃ of curing is placed 24 hours, test physical and mechanical properties, resistant to corrosive media 5wt%NaOH, 5wt%HCl and 3.5wt%NaCl performance, in the NaCl of 3.5wt% solution, test corrosion potential with electrochemical etching method, measure results of property and see Table 1.
Embodiment 2
(1) dihydroxyphenyl propane, Tetrabutyl amonium bromide, trimethylolpropane tris being contracted with the mol ratio is that 1: 0.03: 1.3 and DMF add and have reflux condensing tube, thermometer, stirring arm, N
2In the four-hole bottle of inlet, reacting by heating is after 24 hours in the nitrogen atmosphere, with the reaction system cooling, sink in a large amount of deionized waters the throw out acetone diluted then, anhydrous magnesium sulfate drying spends the night, sal epsom is removed in filtration, and then deposition and purification obtains light yellow transparent liquid shape hyperbranched epoxy resin, weight-average molecular weight 2800 in ether, viscosity 3.5PaS, 1H NMR (DMSO): δ (ppm)=0.765 (CH
3), 1.28 (CH
2), 1.541 (Ph-C (CH
3) 2-Ph), 2.512 (CH
2, epoxy group(ing)), 2.625 (OCH
2, epoxy group(ing)), 3.000 (OCH, epoxy group(ing)), 3.262-3.899 (OCH
2, CH (OH)), 4.960,5.029 (OH), 6.631-7.068 (CH, phenyl ring).IR (KBr) (cm
-1): 3500cm
-1(s, OH), 2945-2870cm
-1(s, CH), 1633-1515cm
-1(s, phenyl ring), 1248-1184cm
-1, 1075-1010cm
-1(s, C-O-C), 908cm
-1(w, epoxy group(ing)).
(2) hyperbranched epoxy resin that will make by step (1), propyl carbinol, pyrroles by content be respectively 75wt%, 5wt%, 20wt% promptly gets the said A component of the present invention after mixing.
The preparation of II .B component
With FeCl
3With the butanone dissolving, add epoxy hardener NX-2041 (the reactive hydrogen equivalent is 82) and mix FeCl
3, butanone and epoxy hardener NX-2041 weight percent be respectively 23wt%, 8wt%, 69wt% and promptly get the said B component of the present invention.
A component and B compositions in weight percentage are mixed, filter at 1: 1, then the gained mixture is coated in metallic surface through oil removing, processing of rust removing, gauge control is about 100 μ m, after room temperature after 80 ℃ of curing is placed 24 hours, test physical and mechanical properties, resistant to corrosive media 5wt%NaOH, 5wt%HCl and 3.5wt%NaCl performance, in the NaCl of 3.5wt% solution, test corrosion potential with electrochemical etching method, measure results of property and see Table 1.
Embodiment 3
(1) Resorcinol, Tetrabutyl amonium bromide, trimethylolpropane tris being contracted with the mol ratio is that 1: 0.05: 1.5 and 250mLDMF add and have reflux condensing tube, thermometer, stirring arm, N
2In the 1000mL four-hole bottle of inlet, reacting by heating is after 24 hours in the nitrogen atmosphere, with the reaction system cooling, sink in a large amount of deionized waters the throw out acetone diluted then, anhydrous magnesium sulfate drying spends the night, sal epsom is removed in filtration, and then deposition and purification obtains light yellow transparent liquid shape hyperbranched epoxy resin in ether, and weight-average molecular weight is 2000, viscosity is 1.8PaS, 1HNMR (DMSO): δ (ppm)=0.765 (CH
3), 1.28 (CH
2), 2.512 (CH
2, epoxy group(ing)), 2.625 (OCH
2, epoxy group(ing)), 3.000 (OCH, epoxy group(ing)), 3.262-3.899 (OCH
2, CH (OH)), 4.960,5.029 (OH), 6.631-7.068 (CH, phenyl).IR (KBr) (cm
-1): 3500cm
-1(s, OH), 2945-2870cm
-1(s, CH), 1633-1515cm
-1(s, phenyl ring), 1248-1184cm
-1, 1075-1010cm
-1(s, C-O-C), 908cm
-1(w, epoxy group(ing)).
(2) will be respectively by content by hyperbranched epoxy resin, the pyrroles that step (1) makes and promptly get the said A component of the present invention after 65wt%, 35wt% mix.
The preparation of II .B component
FeCl3 is dissolved with butanone, add epoxy hardener NX-2041 (the reactive hydrogen equivalent is 82) and mix, FeCl3, butanone and epoxy hardener NX-2041 weight percent are respectively 20wt%, 10wt%, 70wt% and promptly get the said B component of the present invention.
A component and B compositions in weight percentage are mixed, filter at 1.5: 1, then the gained mixture is coated in metallic surface through oil removing, processing of rust removing, gauge control is about 100 μ m, after room temperature after 80 ℃ of curing is placed 24 hours, test physical and mechanical properties, resistant to corrosive media 5wt%NaOH, 5wt%HCl and 3.5wt%NaCl performance, in the NaCl of 3.5wt% solution, test corrosion potential with electrochemical etching method, measure results of property and see Table 1.
Embodiment 4
(1) Bisphenol F, Tetrabutyl amonium bromide, trimethylolpropane tris being contracted with the mol ratio is that 1: 0.03: 1.5 and 250mLDMF add and have reflux condensing tube, thermometer, stirring arm, N
2In the 1000mL four-hole bottle of inlet, reacting by heating is after 18 hours in the nitrogen atmosphere, with the reaction system cooling, sink in a large amount of deionized waters the throw out acetone diluted then, anhydrous magnesium sulfate drying spends the night, sal epsom is removed in filtration, and then deposition and purification obtains light yellow transparent liquid shape hyperbranched epoxy resin in ether, and weight-average molecular weight is 1500, viscosity is 1.3PaS, 1H NMR (DMSO): δ (ppm)=0.765 (CH
3), 1.28 (CH
2), 1.541 (Ph-C (CH
3)
2-Ph), 2.512 (CH
2, epoxy group(ing)), 2.625 (OCH
2, epoxy group(ing)), 3.000 (OCH, epoxy group(ing)), 3.262-3.899 (OCH
2, CH (OH)), 4.960,5.029 (OH), 6.631-7.068 (CH, phenyl ring).IR (KBr) (cm
-1): 3500cm
-1(s, OH), 2945-2870cm
-1(s, CH), 1633-1515cm
-1(s, phenyl ring), 1248-1184cm
-1, 1075-1010cm
-1(s, C-O-C), 908cm
-1(w, epoxy group(ing)).
(2) hyperbranched epoxy resin that will make by step (1), ethanol, pyrroles by content be respectively 60wt%, 10wt%, 30wt% promptly gets the said A component of the present invention after mixing.
The preparation of II .B component
With FeCl
3With the butanone dissolving, add epoxy hardener NX-2041 (the reactive hydrogen equivalent is 82) and mix FeCl
3, butanone and epoxy hardener NX-2041 weight percent be respectively 30wt%, 7wt%, 63wt% and promptly get the said B component of the present invention.
A component and B compositions in weight percentage are mixed, filter at 3: 1, then the gained mixture is coated in metallic surface through oil removing, processing of rust removing, gauge control is about 100 μ m, after room temperature after 80 ℃ of curing is placed 24 hours, test physical and mechanical properties, resistant to corrosive media 5wt%NaOH, 5wt%HCl and 3.5wt%NaCl performance, in the NaCl of 3.5wt% solution, test corrosion potential with electrochemical etching method, measure results of property and see Table 1.
Embodiment 5
(1) bisphenol S, Tetrabutyl amonium bromide, trimethylolpropane tris being contracted with the mol ratio is that 1: 0.04: 1.3 and 250mLDMF add and have reflux condensing tube, thermometer, stirring arm, N
2In the 1000mL four-hole bottle of inlet, reacting by heating is after 24 hours in the nitrogen atmosphere, with the reaction system cooling, sink in a large amount of deionized waters the throw out acetone diluted then, anhydrous magnesium sulfate drying spends the night, sal epsom is removed in filtration, and then deposition and purification obtains light yellow transparent liquid shape hyperbranched epoxy resin in ether, and weight-average molecular weight is 2700, viscosity is 2.0PaS, 1H NMR (DMSO): δ (ppm)=0.765 (CH
3), 1.28 (CH
2), 2.512 (CH
2, epoxy group(ing)), 2.625 (OCH
2, epoxy group(ing)), 3.000 (OCH, epoxy group(ing)), 3.262-3.899 (OCH
2, CH (OH)), 4.960,5.029 (OH), 6.631-7.068 (CH, phenyl).IR (KBr) (cm
-1): 3500cm
-1(s, OH), 2945-2870cm
-1(s, CH), 1633-1515cm
-1(s, phenyl ring), 1248-1184cm
-1, 1162cm
-1(s, S=O) 1075-1010cm
-1(s, C-O-C), 908cm
-1(w, epoxy group(ing)).
(2) hyperbranched epoxy resin that will make by step (1), Virahol, pyrroles by content be respectively 55wt%, 15wt%, 30wt% promptly gets the said A component of the present invention after mixing.
The preparation of II .B component
With FeCl
3With the butanone dissolving, add epoxy hardener NX-2041 (the reactive hydrogen equivalent is 82) and mix FeCl
3, butanone and epoxy hardener NX-2041 weight percent be respectively 72wt%, 8wt%, 20wt% and promptly get the said B component of the present invention.
A component and B compositions in weight percentage are mixed, filter at 1: 1, then the gained mixture is coated in metallic surface through oil removing, processing of rust removing, gauge control is about 100 μ m, after room temperature after 80 ℃ of curing is placed 24 hours, test physical and mechanical properties, resistant to corrosive media 5wt%NaOH, 5wt%HCl and 3.5wt%NaCl performance, in the NaCl of 3.5wt% solution, test corrosion potential with electrochemical etching method, measure results of property and see Table 1.
Embodiment 6
(1) Hydrogenated Bisphenol A, Tetrabutyl amonium bromide, trimethylolpropane tris being contracted with the mol ratio is that 1: 0.04: 1.5 and 250mLDMF add and have reflux condensing tube, thermometer, stirring arm, N
2In the 1000mL four-hole bottle of inlet, reacting by heating is after 24 hours in the nitrogen atmosphere, reaction system is cooled off, sink to then in a large amount of deionized waters, the throw out acetone diluted, anhydrous magnesium sulfate drying spends the night, sal epsom is removed in filtration, and then in ether deposition and purification to obtain light yellow transparent liquid shape hyperbranched epoxy resin weight-average molecular weight be 2200, viscosity is 2.0PaS
1H NMR (DMSO): δ (ppm)=0.765 (CH
3), 1-1.5 (CH
2), 2.512 (CH
2, epoxy group(ing)), 2.625 (OCH
2, epoxy group(ing)), 3.000 (OCH, epoxy group(ing)), 3.262-3.899 (OCH
2, CH (OH)), 4.960,5.029 (OH).IR (KBr) (cm
-1): 3500cm
-1(s, OH), 2945-2870cm
-1(s, CH), 1500cm
-1(s, alicyclic radical), 1248-1184cm
-1, 1075-1010cm
-1(s, C-O-C), 908cm
-1(w, epoxy group(ing)).
(2) hyperbranched epoxy resin that will make by step (1), propyl carbinol, pyrroles by content be respectively 50wt%, 3wt%, 47wt% promptly gets the said A component of the present invention after mixing.
The preparation of II .B component
With FeCl
3With the butanone dissolving, add epoxy hardener NX-2041 and mix FeCl
3, butanone and epoxy hardener NX-2041 weight percent be respectively 60wt%, 10wt%, 30wt% and promptly get the said B component of the present invention.
A component and B compositions in weight percentage are mixed, filter at 1: 1, then the gained mixture is coated in metallic surface through oil removing, processing of rust removing, gauge control is about 100 μ m, after room temperature after 80 ℃ of curing is placed 24 hours, test physical and mechanical properties, resistant to corrosive media 5wt%NaOH, 5wt%HCl and 3.5wt%NaCl performance, in the NaCl of 3.5wt% solution, test corrosion potential with electrochemical etching method, measure results of property and see Table 1.
Table 1 paint film property table
Claims (2)
1. a hyperbranched epoxy resin/polypyrrole composite anticorrosive paint is characterized in that, by weight percentage, raw material comprises following material:
The A component:
Resins, epoxy: 50wt%～80wt%
Pyrroles: 3wt%～50wt%
Thinner: 0～20wt%
The B component:
FeCl
3： 20wt％～80wt％
Solidifying agent: 10wt%～70wt%
Thinner: 1wt%～10wt%
A component and B components by weight (1～3): 1;
Wherein: described Resins, epoxy is hyperbranched epoxy resin, structural formula as structural formula 1 or/and shown in 2;
Described thinner is alcohol or ketone compound; Described solidifying agent is NX-2041, and its reactive hydrogen equivalent is 82;
Described hyperbranched epoxy resin is the hyperbranched epoxy resin that is generated by dihydroxyphenyl propane, Resorcinol, Resorcinol, Bisphenol F, Hydrogenated Bisphenol A or bisphenol S and trihydroxymethylpropanyltri diglycidyl ether;
Described thinner is ethanol, Virahol, propyl carbinol, butanone or acetone;
During use at 80 ℃ of curing hyperbranched epoxy resin/polypyrrole composite anticorrosive paints.
In the said structure formula
2. the preparation method of the hyperbranched epoxy resin/polypyrrole composite anticorrosive paint of claim 1 is characterized in that, may further comprise the steps:
The preparation of I .A component:
(1) contracting above-mentioned bisphenol compound, Tetrabutyl amonium bromide, trimethylolpropane tris with mol ratio is 1: 0.03-0.08: 1.3-1.5 and DMF add and have reflux condensing tube, thermometer, stirring arm, N
2In the reactor of inlet, reacting by heating is after 24 hours in the nitrogen atmosphere, reaction system is cooled off, sink in the deionized water then, throw out acetone diluted then, anhydrous magnesium sulfate drying spends the night, and filter and remove sal epsom, and then deposition and purification obtains light yellow transparent liquid shape hyperbranched epoxy resin in ether;
Above-mentioned bisphenol compound is dihydroxyphenyl propane, Resorcinol, Resorcinol, Bisphenol F, Hydrogenated Bisphenol A or bisphenol S;
(2) will promptly get the A component after mixing by aforementioned weight percent by hyperbranched epoxy resin, thinner, the pyrroles that step (1) makes;
The preparation of II .B component
By aforementioned weight percent, with FeCl
3With the thinner dissolving, the adding epoxy hardener mixes and promptly gets the B component;
III, with A component and B component by weight (1～3): 1 mixes, filters.
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| CN113683777A (en) * | 2021-09-15 | 2021-11-23 | 中国科学院山西煤炭化学研究所 | Preparation method of epoxy-terminated hyperbranched polyether sulfone and application of epoxy-terminated hyperbranched polyether sulfone in salt spray-resistant epoxy resin |
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