CN111925728A - Modified epoxy resin powder coating with high adhesive force - Google Patents
Modified epoxy resin powder coating with high adhesive force Download PDFInfo
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- CN111925728A CN111925728A CN202010851215.XA CN202010851215A CN111925728A CN 111925728 A CN111925728 A CN 111925728A CN 202010851215 A CN202010851215 A CN 202010851215A CN 111925728 A CN111925728 A CN 111925728A
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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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- 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
- 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
- C09D5/03—Powdery paints
- C09D5/033—Powdery paints characterised by the additives
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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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
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- C08K3/22—Oxides; Hydroxides of metals
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- C08K2003/2241—Titanium dioxide
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Abstract
The invention discloses a modified epoxy resin powder coating with high adhesive force, which comprises the following raw materials in parts by weight: 65-80 parts of modified epoxy resin, 15-30 parts of montmorillonite, 10-20 parts of titanium dioxide, 5.5-8 parts of imidazole acid curing agent, 1-2.5 parts of flatting agent and 1-2.5 parts of flatting agent; the preparation method of the powder coating comprises the following steps: weighing the raw materials according to the component weight, adding the raw materials into a mixing barrel, stirring and mixing uniformly, putting the mixture into a screw extruder, extruding, tabletting, crushing by a crusher, and sieving to obtain the powder coating of 15-45 um. The epoxy resin is modified, phosphate groups for improving the adhesive force are introduced, the introduced polar phosphate groups have acidity, and can form a chelating effect and a micro-corrosion effect with the surface of a base material, so that the adhesive force of the cured film on the surfaces of metal, glass and the like can be enhanced, the bonding strength is further improved, and in addition, the epoxy resin containing phosphate ester can form a halogen-free flame-retardant cured film and has a fireproof function.
Description
Technical Field
The invention belongs to the technical field of coatings, and particularly relates to a modified epoxy resin powder coating with high adhesive force.
Background
The epoxy resin molecule contains benzene ring, epoxy group and hydroxyl group, and the main characteristics of the epoxy resin comprise: the photocuring speed is high, the hardness and tensile strength after curing are high, the glossiness of the film layer is high, and the chemical corrosion resistance is excellent. However, the epoxy resin has high viscosity, and after the epoxy resin is prepared into a coating, ink or an adhesive, the consumption of a reactive diluent is high, the cost is high, the curing time is long during the use, the adhesion to a base material is poor after film formation, the bonding strength is low, and the volume shrinkage is large, and particularly when the epoxy resin is coated on the surfaces of various metal objects, the coating is required to have good protective performance and decorative performance, and because the thermal conductivity coefficient of the metal objects is often high, the coating is easy to foam and fall off after being heated, so that the coating with heat resistance and high adhesion has important significance.
Disclosure of Invention
The invention aims to provide a modified epoxy resin powder coating with high adhesive force, which modifies epoxy resin, introduces phosphate ester groups for improving the adhesive force, introduces polar phosphate ester groups with partial acidity, can form a chelating action and a micro-corrosion action with the surface of a base material, can enhance the adhesive force of a cured film on the surfaces of metal, glass and the like, and further improves the bonding strength, and in addition, the epoxy resin containing phosphate ester can form a halogen-free flame-retardant cured film, improves the stability of a coating, and has a fireproof function.
The purpose of the invention can be realized by the following technical scheme:
a modified epoxy resin powder coating with high adhesion comprises the following raw materials in parts by weight: 65-80 parts of modified epoxy resin, 15-30 parts of montmorillonite, 10-20 parts of titanium dioxide, 5.5-8 parts of imidazole acid curing agent, 1-2.5 parts of flatting agent and 1-2.5 parts of flatting agent;
the preparation method of the modified epoxy resin comprises the following steps:
first step, preparation of modifier
S1, adding 0.20mol of 1,1,1,3,5,5, 5-heptamethyltrisiloxane bis (trimethylsiloxy) methylsilane, 0.21-0.23mol of allyl polyoxyethylene ether and 1L of solvent dioxane into a three-neck flask connected with a reflux device, introducing inert gas nitrogen into the three-neck flask for 10-15min, adding a catalyst into a nitrogen atmosphere, continuously introducing nitrogen for 10-15min, closing the nitrogen, heating to 105-110 ℃, carrying out reflux reaction for 4-6h, after the reaction is finished, carrying out reduced pressure distillation to remove the solvent, washing with diethyl ether, and drying to obtain an anhydrous modified intermediate A1;
s2, adding 50mmol of phosphorus oxychloride, 100-105mmol of modified intermediate A1, 15-20ml of triethylamine and 500ml of solvent toluene into a four-neck flask provided with a thermometer, a stirrer and a reflux device, transferring the flask into a water bath kettle, keeping the temperature and stirring for 2-3h at 30-35 ℃, after the reaction is finished, removing the water bath kettle, transferring the reaction liquid into a separating funnel, adding 300-400ml of 20-30% sodium carbonate aqueous solution with the mass fraction of 20-30% into the separating funnel, fully mixing and washing, collecting an organic phase, performing liquid separation and washing on the organic phase for 2-3 times by using distilled water, removing the residual ammonium salt, performing reduced pressure distillation on the organic phase after water washing to remove the solvent, and drying to obtain the modifier shown in the formula A2;
second step, preparation of modified epoxy resin
Adding epoxy resin into a reaction kettle, heating to 55-60 ℃ while stirring, then adding a modifier A2 and a catalyst diphenylphosphine ferrocene, and adding
And placing the reaction kettle in a water bath kettle, reacting for 2-3h at the temperature of 75-80 ℃, and naturally cooling to room temperature after the reaction is finished to obtain the modified epoxy resin.
Further, in step S1, the catalyst is RuCl, a ruthenium catalyst2(PPh3)3The addition amount of the ruthenium catalyst is 3-5 mmol.
Further, in the second step, the mass ratio of the epoxy resin, the modifier A2 and the catalyst diphenylphosphine ferrocene is 10:3-5: 0.01.
Further, the structural formula of the imidazole curing agent is shown as formula Q:
the preparation method of the imidazole curing agent comprises the following steps: weighing 1.7g of 2, 5-thiophenedicarboxylic acid, 2.2-2.5g of o-phenylenediamine and an acid catalyst, adding the materials into a small-sized high-pressure reaction kettle, transferring the reaction kettle into a microwave oven, radiating the materials for 5-7min under the power of 550-700W, removing the microwave oven after the reaction is finished, adding 50ml of deionized water into the reaction kettle, stirring the mixture for 10-15min, standing the mixture for half an hour, filtering the mixture, putting the filtered mixture into 100ml of 35-40% sodium hydroxide solution by mass fraction, stirring the mixture for 10-15min, filtering the filtered mixture, washing the filtered mixture with deionized water, and recrystallizing the deionized water by adopting anhydrous ether to obtain the imidazole curing agent of the formula Q.
Further, the acid catalyst is 0.15-0.2g of phosphotungstic acid and 5ml of polyphosphoric acid.
Further, the leveling agent is dimethyl polysiloxane.
Further, the matting agent is one of sodium stearate, magnesium stearate and potassium stearate.
Further, the preparation method of the powder coating comprises the following steps: weighing the raw materials according to the component weight, adding the raw materials into a mixing barrel, stirring and mixing uniformly, putting the mixture into a screw extruder, extruding, tabletting, crushing by a crusher, and sieving to obtain the powder coating of 15-45 um.
The invention has the beneficial effects that:
the invention provides a modified epoxy resin powder coating with high adhesive force, which modifies epoxy resin and introduces phosphate groups for improving the adhesive force, and specifically comprises the following steps: firstly, a modifier is prepared, 1,1,1,3,5,5, 5-heptamethyltrisiloxane bistrimethylsiloxysilane and allyl polyoxyethylene ether are used as initial raw materials, and RuCl is used as a ruthenium catalyst2(PPh3)3Carrying out addition reaction under the action of (1) to obtain a modified intermediate A1, carrying out substitution reaction on one equivalent of phosphorus oxychloride and 2 equivalents of modified intermediate A1 in an alkaline environment, hydrolyzing by using a sodium carbonate aqueous solution to obtain a modifier, and finally carrying out ring-opening esterification reaction on the epoxy resin and the modifier under the action of a catalyst diphenylphosphine ferrocene, wherein the modifier is further bonded into the epoxy resin; the modified epoxy resin contains a flexible chain segment with a modifier structure and an end group of organosilicon, the flexible chain segment increases the contact chance with a reaction group, increases the compatibility of the modified epoxy resin and a coating system and improves the coating performanceMechanical properties; the introduced polar phosphate group has a partial acidity, can form a chelating effect and a micro-corrosion effect with the surface of a base material, can enhance the adhesive force of the cured film to the surfaces of metal, glass and the like, and further improves the bonding strength, and in addition, the epoxy resin containing phosphate ester can form a halogen-free flame-retardant cured film, improves the stability of the coating, and has a fireproof function.
Of course, it is not necessary for any product in which the invention is practiced to achieve all of the above-described advantages at the same time.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings used in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present invention, and it is obvious for those skilled in the art that other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a reaction scheme of modified intermediate A1 according to the present invention;
FIG. 2 is a reaction scheme of a modifier according to the present invention;
FIG. 3 shows a reaction formula for synthesizing a modified epoxy resin according to the present invention.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The preparation method of the imidazole curing agent comprises the following steps: weighing 1.7g of 2, 5-thiophenedicarboxylic acid, 2.4g of o-phenylenediamine, 0.2g of phosphotungstic acid and 5ml of polyphosphoric acid, adding the weighed materials into a small-sized high-pressure reaction kettle, transferring the reaction kettle into a microwave oven, radiating the reaction kettle for 5min under the power of 600W, removing the microwave oven after the reaction is finished, adding 50ml of deionized water into the reaction kettle, stirring the mixture for 15min, standing the mixture for half an hour, filtering the mixture, putting the filtered product into 100ml of a sodium hydroxide solution with the mass fraction of 40%, stirring the solution for 10min, filtering the solution, washing the filtered product with the deionized water, and recrystallizing the product by using anhydrous ether to obtain the imidazole curing agent with;
the detection result is that the following substances are obtained by GC-MS: imidazole curing agent (C)18H12N4S) has a molecular weight of 316.178.
Example 2
As shown in fig. 1-3, the preparation method of the modified epoxy resin comprises the following steps:
first step, preparation of modifier
S1, adding 0.20mol of 1,1,1,3,5,5, 5-heptamethyltrisiloxane bis (trimethylsiloxy) methylsilane, 0.21mol of allyl polyoxyethylene ether and 1L of solvent dioxane into a three-neck flask connected with a reflux device, introducing inert gas nitrogen into the three-neck flask for 15min, and adding 5mmol of ruthenium catalyst RuCl into a nitrogen atmosphere2(PPh3)3Continuously introducing nitrogen for 15min, closing the nitrogen, heating to 105 ℃, carrying out reflux reaction for 5h, after the reaction is finished, carrying out reduced pressure distillation to remove the solvent, washing with anhydrous ether, and drying to obtain a modified intermediate A1; the yield is 85.4%;
s2, adding 50mmol of phosphorus oxychloride, 103mmol of modified intermediate A1, 17ml of triethylamine and 500ml of solvent toluene into a four-neck flask provided with a thermometer, a stirrer and a reflux device, transferring the flask into a water bath, keeping the temperature and stirring for 3 hours at 35 ℃, after the reaction is finished, removing the water bath, transferring the reaction liquid into a separating funnel, adding 400ml of sodium carbonate aqueous solution with the mass fraction of 30% into the separating funnel, fully mixing and washing to ensure that phosphate acyl chloride is fully hydrolyzed and converted into phosphate, removing most of ammonium salt in the separating process, collecting an organic phase, carrying out separating washing on the organic phase for 2-3 times by using finishing water, removing the residual ammonium salt, carrying out reduced pressure distillation on the organic phase after water washing to remove the solvent, and drying to obtain the modifier shown in the formula A2; the yield is 86.3%;
second step, preparation of modified epoxy resin
Adding 10g of epoxy resin into a reaction kettle, heating to 60 ℃ while stirring, then adding 3.5g of modifier A2 and 0.01g of catalyst diphenylphosphine ferrocene, placing the reaction kettle into a water bath kettle after the addition is finished, reacting for 2 hours at the temperature of 80 ℃, and naturally cooling to room temperature after the reaction is finished to obtain the modified epoxy resin;
infrared characterization
The infrared characterization of the modified epoxy resin is as follows: IR (KBr):
3032-3004 (benzene ring), 2986-2865 (-CH)2),1286(P＝O),932(-O-Si-)cm-1。
Example 3
A modified epoxy resin powder coating with high adhesion comprises the following raw materials in parts by weight: 70g of modified epoxy resin, 22g of montmorillonite, 10g of titanium dioxide, 6g of imidazole acid curing agent, 1g of flatting agent and 1g of flatting agent;
the flatting agent is dimethyl polysiloxane;
the flatting agent is sodium stearate;
the preparation method of the powder coating comprises the following steps: weighing the raw materials according to the component weight, adding the raw materials into a mixing barrel, stirring and mixing uniformly, putting the mixture into a screw extruder, extruding, tabletting, crushing by a crusher, and sieving to obtain the powder coating of 15-45 um.
Example 4
A modified epoxy resin powder coating with high adhesion comprises the following raw materials in parts by weight: 65g of modified epoxy resin, 15g of montmorillonite, 20g of titanium dioxide, 8g of imidazole acid curing agent, 2g of flatting agent and 2g of flatting agent;
the flatting agent is dimethyl polysiloxane;
the delustering agent is magnesium stearate;
the preparation method of the powder coating comprises the following steps: weighing the raw materials according to the component weight, adding the raw materials into a mixing barrel, stirring and mixing uniformly, putting the mixture into a screw extruder, extruding, tabletting, crushing by a crusher, and sieving to obtain the powder coating of 15-45 um.
Example 5
A modified epoxy resin powder coating with high adhesion comprises the following raw materials in parts by weight: 80g of modified epoxy resin, 30g of montmorillonite, 14g of titanium dioxide, 7g of imidazole acid curing agent, 1.5g of flatting agent and 1.5g of flatting agent;
the flatting agent is dimethyl polysiloxane;
the flatting agent is potassium stearate;
the preparation method of the powder coating comprises the following steps: weighing the raw materials according to the component weight, adding the raw materials into a mixing barrel, stirring and mixing uniformly, putting the mixture into a screw extruder, extruding, tabletting, crushing by a crusher, and sieving to obtain the powder coating of 15-45 um.
Comparative example 1
The modified epoxy resin was replaced with an epoxy resin, and the rest was the same as in example 5.
The powder coatings in examples 3-5 and comparative example 1 were sprayed onto steel plate samples by electrostatic spraying, baked at 210 ℃ for 5 minutes to obtain films with a thickness of 60um, and the performance of each film was tested, as shown in table one;
the performance test method and evaluation criteria of the coating film are as follows:
the leveling evaluation standard of the coating film is used for carrying out leveling rating according to a leveling effect rating standard plate of the American PCI, wherein 1 is poor, and 10 is excellent;
the glossiness test of the coating film refers to the national standard GB/T9754;
the adhesive force of the coating film refers to the national standard GB/T9286-1998 test for marking the grids of paint films of colored paint and varnish (0-5 grade, the best grade 0, the worst grade 5);
the impact strength of the coating film is according to the national standard GB/T1732;
the transparency of the coating is transparent according to national standard GB/T1721, 82-100, slightly turbid 52-81 and turbid below 51;
table one: results of Performance test of coating film
The foregoing is merely exemplary and illustrative of the principles of the present invention and various modifications, additions and substitutions of the specific embodiments described herein may be made by those skilled in the art without departing from the principles of the present invention or exceeding the scope of the claims set forth herein.
Claims (8)
1. A modified epoxy resin powder coating with high adhesion is characterized in that: the feed comprises the following raw materials in parts by weight: 65-80 parts of modified epoxy resin, 15-30 parts of montmorillonite, 10-20 parts of titanium dioxide, 5.5-8 parts of imidazole acid curing agent, 1-2.5 parts of flatting agent and 1-2.5 parts of flatting agent;
the preparation method of the modified epoxy resin comprises the following steps:
first step, preparation of modifier
S1, adding 0.20mol of 1,1,1,3,5,5, 5-heptamethyltrisiloxane bis (trimethylsiloxy) methylsilane, 0.21-0.23mol of allyl polyoxyethylene ether and 1L of solvent dioxane into a three-neck flask connected with a reflux device, introducing inert gas nitrogen into the three-neck flask for 10-15min, adding a catalyst into a nitrogen atmosphere, continuously introducing nitrogen for 10-15min, closing the nitrogen, heating to 105-110 ℃, carrying out reflux reaction for 4-6h, after the reaction is finished, carrying out reduced pressure distillation to remove the solvent, washing with diethyl ether, and drying to obtain an anhydrous modified intermediate A1;
s2, adding 50mmol of phosphorus oxychloride, 100-105mmol of modified intermediate A1, 15-20ml of triethylamine and 500ml of solvent toluene into a four-neck flask provided with a thermometer, a stirrer and a reflux device, transferring the flask into a water bath kettle, keeping the temperature and stirring for 2-3h at 30-35 ℃, after the reaction is finished, removing the water bath kettle, transferring the reaction liquid into a separating funnel, adding 300-400ml of 20-30% sodium carbonate aqueous solution with the mass fraction of 20-30% into the separating funnel, fully mixing and washing, collecting an organic phase, performing liquid separation and washing on the organic phase for 2-3 times by using distilled water, removing the residual ammonium salt, performing reduced pressure distillation on the organic phase after water washing to remove the solvent, and drying to obtain the modifier shown in the formula A2;
second step, preparation of modified epoxy resin
Adding epoxy resin into a reaction kettle, heating to 55-60 ℃ while stirring, then adding a modifier A2 and a catalyst diphenylphosphine ferrocene, placing the reaction kettle into a water bath kettle after the addition is finished, reacting for 2-3h at the temperature of 75-80 ℃, and naturally cooling to room temperature after the reaction is finished to obtain the modified epoxy resin.
2. The modified epoxy resin powder coating with high adhesion as claimed in claim 1, wherein: in step S1, the catalyst is ruthenium catalyst RuCl2(PPh3)3The addition amount of the ruthenium catalyst is 3-5 mmol.
3. The modified epoxy resin powder coating with high adhesion as claimed in claim 1, wherein: in the second step, the mass ratio of the epoxy resin, the modifier A2 and the catalyst diphenylphosphine ferrocene is 10:3-5: 0.01.
4. The modified epoxy resin powder coating with high adhesion as claimed in claim 1, wherein: the structural formula of the imidazole curing agent is shown as formula Q:
the preparation method of the imidazole curing agent comprises the following steps: weighing 1.7g of 2, 5-thiophenedicarboxylic acid, 2.2-2.5g of o-phenylenediamine and an acid catalyst, adding the materials into a small-sized high-pressure reaction kettle, transferring the reaction kettle into a microwave oven, radiating the materials for 5-7min under the power of 550-700W, removing the microwave oven after the reaction is finished, adding 50ml of deionized water into the reaction kettle, stirring the mixture for 10-15min, standing the mixture for half an hour, filtering the mixture, putting the filtered mixture into 100ml of 35-40% sodium hydroxide solution by mass fraction, stirring the mixture for 10-15min, filtering the filtered mixture, washing the filtered mixture with deionized water, and recrystallizing the deionized water by adopting anhydrous ether to obtain the imidazole curing agent of the formula Q.
5. The modified epoxy resin powder coating with high adhesion as claimed in claim 4, wherein: the acid catalyst is 0.15-0.2g phosphotungstic acid and 5ml polyphosphoric acid.
6. The modified epoxy resin powder coating with high adhesion as claimed in claim 1, wherein: the leveling agent is dimethyl polysiloxane.
7. The modified epoxy resin powder coating with high adhesion as claimed in claim 1, wherein: the matting agent is one of sodium stearate, magnesium stearate and potassium stearate.
8. The modified epoxy resin powder coating with high adhesion as claimed in claim 1, wherein: the preparation method of the powder coating comprises the following steps: weighing the raw materials according to the component weight, adding the raw materials into a mixing barrel, stirring and mixing uniformly, putting the mixture into a screw extruder, extruding, tabletting, crushing by a crusher, and sieving to obtain the powder coating of 15-45 um.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116284652A (en) * | 2023-03-10 | 2023-06-23 | 河北乾海管道制造有限公司 | Steel sleeve steel polyurethane heat-insulating pipe and preparation method thereof |
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| CN107722237A (en) * | 2017-11-07 | 2018-02-23 | 天津工业大学 | A kind of water-soluble phosphoric acid ester type bisphenol A epoxide resin and preparation method thereof |
| CN111040457A (en) * | 2019-12-27 | 2020-04-21 | 田朝义 | Preparation method of curing coated flame-retardant waterproof agent for plastics |
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| CN101747826A (en) * | 2009-11-27 | 2010-06-23 | 广州擎天实业有限公司 | Low temperature curing epoxy low-gloss powder coating and preparation method thereof |
| CN104448237A (en) * | 2014-11-05 | 2015-03-25 | 广东一通管业科技有限公司 | Silicon-nitrogen-phosphate coordinating flame retardant epoxy resin powder coating suitable for steel tube and preparation method of silicon-nitrogen-phosphate coordinating flame retardant epoxy resin powder coating |
| CN107722237A (en) * | 2017-11-07 | 2018-02-23 | 天津工业大学 | A kind of water-soluble phosphoric acid ester type bisphenol A epoxide resin and preparation method thereof |
| CN111040457A (en) * | 2019-12-27 | 2020-04-21 | 田朝义 | Preparation method of curing coated flame-retardant waterproof agent for plastics |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116284652A (en) * | 2023-03-10 | 2023-06-23 | 河北乾海管道制造有限公司 | Steel sleeve steel polyurethane heat-insulating pipe and preparation method thereof |
| CN116284652B (en) * | 2023-03-10 | 2023-08-08 | 河北乾海管道制造有限公司 | Steel sleeve steel polyurethane heat-insulating pipe and preparation method thereof |
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Application publication date: 20201113 |