CN108727563B - Epoxy curing agent - Google Patents
Epoxy curing agent Download PDFInfo
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- CN108727563B CN108727563B CN201710257032.3A CN201710257032A CN108727563B CN 108727563 B CN108727563 B CN 108727563B CN 201710257032 A CN201710257032 A CN 201710257032A CN 108727563 B CN108727563 B CN 108727563B
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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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
- C08G59/623—Aminophenols
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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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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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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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
Abstract
The invention provides an epoxy curing agent. The epoxy curing agent comprises the following components in parts by weight in a synthesis formula: 10-80 parts of epoxy resin, 5-70 parts of organic phenol, 0.005-9 parts of catalyst, 5-60 parts of amine substance and 1-150 parts of solvent. According to the invention, the epoxy curing agent modified by organic phenol has good miscibility with epoxy resin, so that the obtained coating film has high gloss, and meanwhile, the epoxy curing agent and the epoxy resin react to form a large molecular weight bodily structure, so that the corrosion resistance and the medium resistance of the coating film are improved. In addition, the organic phenol is introduced, so that the flexibility and the hydrophobicity of the coating film are improved, the reaction speed of the epoxy resin and the epoxy curing agent is controlled, and the construction time limit is prolonged.
Description
Technical Field
The invention relates to the technical field of water-based paint, and particularly relates to an epoxy curing agent.
Background
The waterborne epoxy resin has excellent corrosion resistance and medium resistance and is widely applied in actual production, but the epoxy resin has poor flexibility and small molecular weight, and a curing agent needs to be matched in the using process to prepare a coating film with good resistance. Because the structural difference between the epoxy resin and the curing agent is large, the problems of low coating film gloss, poor performance and the like often occur in the application process. In addition, the epoxy group has high activity, fast reaction with curing agent, short service life and inconvenient application.
Disclosure of Invention
In view of the above, the invention provides an epoxy curing agent, and aims to solve the problems of low gloss, poor performance and short service life of the existing epoxy resin coating.
In one aspect, the invention provides an epoxy curing agent, which comprises the following components in parts by weight in a synthesis formula: 10-80 parts of epoxy resin, 5-70 parts of organic phenol, 0.005-9 parts of catalyst, 5-60 parts of amine substance and 1-150 parts of solvent.
Further, in the epoxy curing agent, the synthetic formula comprises the following components in parts by weight: 20-50 parts of epoxy resin, 10-50 parts of organic phenol, 0.01-5 parts of catalyst, 10-50 parts of amine substance and 1-110 parts of solvent.
Further, in the epoxy curing agent, the epoxy resin is at least one selected from the group consisting of bisphenol a type epoxy resin, bisphenol F type epoxy resin and bisphenol S type epoxy resin having an epoxy equivalent of 50 to 800.
In the epoxy curing agent, the organic phenol is at least one selected from the group consisting of petroleum phenol, cashew nutshell phenol, nonyl phenol and phenol.
Further, in the epoxy hardener, the catalyst is at least one selected from the group consisting of dimethylethanolamine, N-dimethylbenzylamine, potassium persulfate, triphenylphosphine, and boron trifluoride.
In the epoxy curing agent, the amine substance is at least one selected from diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine and polyethylenepolyamine.
In the epoxy hardener, the solvent is at least one selected from the group consisting of ethanol, isopropyl alcohol, ethylene glycol monobutyl ether, propylene glycol methyl ether, water, glacial acetic acid, and glycidyl versatate.
On the other hand, the invention also provides a preparation method of the epoxy curing agent, which comprises the following steps: (1) weighing epoxy resin, organic phenol and a catalyst in the formula, adding the epoxy resin, the organic phenol and the catalyst into a reaction container, heating to 75-250 ℃, preserving heat for 0.5-7 hours, cooling to 30-120 ℃, adding 1-75 parts of solvent in the formula to obtain an adduct of the epoxy resin and the organic phenol, and discharging; (2) adding amine substances and 1-60 parts of solvent in the formula into the reaction container, heating to 40-125 ℃, slowly dropwise adding the adduct of the epoxy resin obtained in the step (1) and the organic phenol under the stirring state, and preserving the heat at 70-135 ℃ for 0.4-6 hours; (3) slowly adding the residual solvent in the formula, and stirring for 5-100 minutes to obtain the epoxy curing agent.
According to the invention, the epoxy curing agent modified by organic phenol has good miscibility with epoxy resin, so that the obtained coating film has high gloss, and meanwhile, the epoxy curing agent and the epoxy resin react to form a large molecular weight bodily structure, so that the corrosion resistance and the medium resistance of the coating film are improved. In addition, the organic phenol is introduced, so that the flexibility and the hydrophobicity of the coating film are improved, the reaction speed of the epoxy resin and the epoxy curing agent is controlled, and the construction time limit is prolonged.
Detailed Description
For a further understanding of the invention, preferred embodiments of the invention are described below in conjunction with the examples, but it should be understood that these descriptions are included merely to further illustrate the features and advantages of the invention and are not intended to limit the invention to the claims.
The invention provides an epoxy curing agent, which comprises the following components in parts by weight in a synthesis formula: 10-80 parts of epoxy resin, 2-70 parts of organic phenol, 0.005-9 parts of catalyst, 5-60 parts of amine substance and 1-150 parts of solvent. Preferably, the synthetic formula comprises the following components in parts by weight: 20-50 parts of epoxy resin, 10-50 parts of organic phenol, 0.01-5 parts of catalyst, 10-50 parts of amine substance and 1-110 parts of solvent.
Wherein the epoxy resin is at least one selected from bisphenol A type epoxy resin, bisphenol F type epoxy resin and bisphenol S type epoxy resin with the epoxy equivalent of 50-800. Preferably, the epoxy resin is selected from bisphenol A type epoxy resin with epoxy equivalent of 150-500, bisphenol F and bisphenol S type epoxy resin with epoxy equivalent of 100-800. For example, the bisphenol a epoxy resin may be E51 type epoxy resin, E44 type epoxy resin, or the like; the bisphenol F type epoxy resin may be NPEF170 type epoxy resin, EPIKOTE862 type epoxy resin, or the like.
The organic phenol is at least one selected from petroleum phenol, cashew nutshell phenol, nonyl phenol and phenol. The organic phenol modifies the epoxy resin, and introduces phenolic hydroxyl with long carbon chain, thereby increasing the flexibility of the reaction product.
The catalyst is at least one selected from dimethylethanolamine, N dimethylbenzylamine, potassium persulfate, triphenylphosphine and boron trifluoride.
The amine substance is at least one selected from diethylenetriamine, triethylene tetramine, tetraethylene pentamine, pentaethylene hexamine and polyethylene polyamine. Wherein, the polyethylene polyamine is a coproduct of ethylenediamine, diethylenetriamine, triethylenetetramine and tetraethylenepentamine.
The solvent is at least one selected from ethanol, isopropanol, ethylene glycol monobutyl ether, propylene glycol methyl ether, water, glacial acetic acid and tert-carbonic acid glycidyl ether.
The raw materials used in the examples of the present invention are not particularly limited in their source, and may be commercially available.
The invention also provides a preparation method of the epoxy curing agent, which comprises the following steps:
(1) weighing the epoxy resin, the organic phenol and the catalyst in the formula, adding the epoxy resin, the organic phenol and the catalyst into a reaction container, heating to 75-250 ℃, keeping the temperature for 0.5-7 hours, cooling to 30-120 ℃, adding 1-75 parts of solvent to obtain an adduct of the epoxy resin and the organic phenol, and discharging. Preferably, the heating temperature is 90-200 ℃, the heat preservation time is 1-5 hours, and the cooling temperature is 40-100 ℃. By introducing the organic phenolic substance, the flexibility and the water resistance of the curing agent are improved.
(2) Adding amine substances and 1-60 parts of solvent in the formula into the reaction container, heating to 40-125 ℃, slowly adding the adduct of the epoxy resin and the organic phenol obtained in the step (1) under the stirring state, and keeping the temperature at 70-135 ℃ for 0.4-6 hours. Preferably, the heating temperature is 50-120 ℃, the heat preservation temperature is 80-120 ℃, and the heat preservation time is 1-5 hours. The activity of the curing agent is controlled through the step, so that the service life of the mixed curing agent and epoxy resin is prolonged.
(3) Adding the rest solvent in the formula, and stirring for 5-100 minutes to obtain the epoxy curing agent. Preferably, the stirring time is 10 to 50 minutes. The viscosity of the curing agent is adjusted through the step (3) so as to be convenient to use.
According to the invention, the epoxy curing agent modified by organic phenol has good miscibility with epoxy resin, so that the obtained coating film has high gloss, and meanwhile, the epoxy curing agent and the epoxy resin react to form a large molecular weight bodily structure, so that the corrosion resistance and the medium resistance of the coating film are improved. In addition, the organic phenol is introduced, so that the flexibility and the hydrophobicity of the coating film are improved, the reaction speed of the epoxy resin and the epoxy curing agent is controlled, and the construction time limit is prolonged.
The present invention is further illustrated by the following specific examples.
Example 1
(1) Adding 35 g of E51 epoxy resin, 22 g of cashew nut shell phenol and 0.1 g of N, N dimethylbenzylamine into a three-neck bottle, heating to 100 ℃, preserving heat for 2h, cooling to 80 ℃, adding 10 g of tertiary carbonic acid glycidyl ether to obtain an adduct of the epoxy resin and the cashew nut shell phenol, and discharging;
(2) adding 20 g of diethylenetriamine and 5 g of ethylene glycol monobutyl ether into a three-necked bottle, heating to 70 ℃, then dropwise adding the product synthesized in the step (1), and preserving heat for 2 hours at 80 ℃ after dropwise adding;
(3) and slowly adding 8 g of water, and stirring for 30 minutes to obtain the epoxy curing agent.
Example 2
(1) Adding 20 g of bisphenol F type epoxy resin (NPEF170), 37 g of petroleum phenol and 0.05 g of N, N dimethyl benzylamine into a three-neck bottle, heating to 90 ℃, keeping the temperature for 1h, cooling to 40 ℃, adding 15 g of ethylene glycol monobutyl ether to obtain an adduct of the epoxy resin and the petroleum phenol, and discharging;
(2) adding 20 g of tetraethylenepentamine and 60 g of ethylene glycol monobutyl ether into a three-necked bottle, heating to 50 ℃, then dropwise adding the product synthesized in the step (1), and keeping the temperature at 100 ℃ for 1h after dropwise adding;
(3) slowly adding 40 g of glacial acetic acid, and stirring for 30 minutes to obtain the epoxy curing agent.
Example 3
(1) Adding 50 g of a mixture of E51 epoxy resin and bisphenol F type epoxy resin (NPEF170), 12 g of phenol and 0.1 g of N, N dimethyl benzylamine into a three-neck flask, heating to 200 ℃, keeping the temperature for 0.5h, cooling to 40 ℃, adding 5 g of ethylene glycol monobutyl ether, obtaining an adduct of the epoxy resin and the phenol, and discharging;
(2) adding 20 g of tetraethylenepentamine and 5 g of ethylene glycol monobutyl ether into a three-necked bottle, heating to 70 ℃, then dropwise adding the product synthesized in the step (1), and preserving heat for 1.5 hours at 80 ℃ after dropwise adding;
(3) slowly adding 8 g of glacial acetic acid, and stirring for 30 minutes to obtain the epoxy curing agent.
Example 4
(1) Adding 20 g of E51 epoxy resin, 32 g of petroleum phenol and 0.01 g of triphenyl phosphine into a three-necked bottle, heating to 135 ℃, preserving heat for 5h, cooling to 120 ℃, adding 10 g of propylene glycol monomethyl ether to obtain an adduct of the epoxy resin and the petroleum phenol, and discharging;
(2) adding 20 g of diethylenetriamine and 5 g of ethylene glycol monobutyl ether into a three-necked bottle, heating to 100 ℃, then dropwise adding the product synthesized in the step (1), and preserving heat for 2 hours at 120 ℃ after dropwise adding;
(3) slowly adding 10 g of glacial acetic acid, and stirring for 30 minutes to obtain the epoxy curing agent.
Example 5
(1) Adding 25 g of E44 epoxy resin, 27 g of a mixture of cashew nutshell phenol and petroleum phenol and 0.5 g of N, N-dimethylbenzylamine into a three-neck bottle, heating to 85 ℃, keeping the temperature for 4h, cooling to 30 ℃, adding 10 g of ethylene glycol monobutyl ether to obtain an adduct of the epoxy resin and the cashew nutshell phenol, and discharging;
(2) adding 20 g of tetraethylenepentamine and 8 g of ethylene glycol monobutyl ether into a three-necked bottle, heating to 125 ℃, then dropwise adding the product synthesized in the step (1), and preserving heat for 3 hours at 135 ℃ after dropwise adding;
(3) slowly adding 10 g of propylene glycol methyl ether, and stirring for 5 minutes to obtain the epoxy curing agent.
Example 6
(1) Adding 10 g of E51 epoxy resin, 22 g of cashew nut shell phenol and 9 g of N, N dimethylbenzylamine into a three-neck bottle, heating to 200 ℃, preserving heat for 0.5h, cooling to 60 ℃, adding 10 g of tertiary carbonic acid glycidyl ether, obtaining an adduct of the epoxy resin and the cashew nut shell phenol, and discharging;
(2) adding 10 g of diethylenetriamine and 5 g of ethylene glycol monobutyl ether into a three-necked bottle, heating to 90 ℃, then dropwise adding the product synthesized in the step (1), and preserving heat for 6 hours at 105 ℃ after dropwise adding;
(3) slowly adding 20 g of ethanol, and stirring for 100 minutes to obtain the epoxy curing agent.
Example 7
(1) Adding 45 g of E44 epoxy resin, 30 g of a mixture of cashew nutshell phenol and nonyl phenol and 5 g of triphenyl phosphorus into a three-necked bottle, heating to 200 ℃, keeping the temperature for 0.8h, cooling to 80 ℃, adding 60 g of tertiary carbonic acid glycidyl ether to obtain an adduct of the epoxy resin and the cashew nutshell phenol, and discharging;
(2) adding 50 g of diethylenetriamine and 30 g of ethylene glycol monobutyl ether into a three-necked bottle, heating to 120 ℃, then dropwise adding the product synthesized in the step (1), and preserving heat for 0.4h at 125 ℃ after dropwise adding;
(3) slowly adding 20 g of isopropanol, and stirring for 40 minutes to obtain the epoxy curing agent.
Example 8
(1) Adding 80 g of E51 epoxy resin, 50 g of a mixture of nonyl phenol and 0.005 g of dimethylethanolamine into a three-neck flask, heating to 250 ℃, keeping the temperature for 0.6h, cooling to 100 ℃, adding 10 g of tertiary carbonic acid glycidyl ether to obtain an adduct of epoxy resin and nonyl phenol, and discharging;
(2) adding 5 g of diethylenetriamine and 6 g of ethylene glycol monobutyl ether into a three-necked bottle, heating to 65 ℃, then dropwise adding the product synthesized in the step (1), and preserving heat for 6 hours at 90 ℃ after dropwise adding;
(3) slowly adding 10 g of water, and stirring for 50 minutes to obtain the epoxy curing agent.
Example 9
(1) Adding 30 g of bisphenol F type epoxy resin (EPIKOTE862), 5 g of cashew nut shell phenol and 0.008 g of boron trifluoride into a three-neck flask, heating to 220 ℃, keeping the temperature for 0.7h, cooling to 50 ℃, adding 0.3 g of tertiary carbonic acid glycidyl ether to obtain an adduct of the epoxy resin and the cashew nut shell phenol, and discharging;
(2) adding 50 g of a mixture of triethylene tetramine and diethylenetriamine into a three-necked bottle, heating 0.3 g of tertiary carbonic acid glycidyl ether to 40 ℃, then dropwise adding the product synthesized in the step (1), and preserving heat for 5 hours at 85 ℃ after dropwise adding;
(3) slowly adding 0.4 g of tertiary carbonic acid glycidyl ether, and stirring for 30 minutes to obtain the epoxy curing agent.
Example 10
(1) Adding 40 g of E44 epoxy resin, 70 g of cashew nut shell phenol and 4 g of potassium persulfate into a three-neck flask, heating to 75 ℃, keeping the temperature for 7h, cooling to 60 ℃, adding 55 g of ethylene glycol monobutyl ether to obtain an adduct of the epoxy resin and the cashew nut shell phenol, and discharging;
(2) adding 60 g of a mixture of tetraethylenepentamine and pentaethylenehexamine into a three-necked bottle, heating 45 g of ethylene glycol monobutyl ether to 50 ℃, then dropwise adding the product synthesized in the step (1), and preserving heat for 3 hours at 120 ℃ after dropwise adding;
(3) slowly adding 50 g of ethylene glycol monobutyl ether, and stirring for 10 minutes to obtain the epoxy curing agent.
After the epoxy curing agent provided in the above examples 1 to 10 was mixed with the aqueous epoxy emulsion, a performance test was performed, wherein the ratio of the curing agent to the epoxy resin (EP 203 resin, beijing sunshine sinder environmental protection technology ltd) was calculated according to the theory, that is: the ratio of the mole number of epoxy groups to the mole number of active hydrogen in the curing agent is 1:1, the test environment is a standard environment, namely: the temperature is 23-25 ℃, and the humidity is 50-55; the test substrate is a carbon steel plate, the film thickness is 65 microns, the test substrate is baked for 30 minutes at 80 ℃, and the film coating performance is tested after the test substrate is maintained for 7 days in a standard environment. The results are shown in Table 1:
it will be apparent to those skilled in the art that various changes and modifications may be made in the present invention without departing from the spirit and scope of the invention. Thus, if such modifications and variations of the present invention fall within the scope of the claims of the present invention and their equivalents, the present invention is also intended to include such modifications and variations.
Claims (1)
1. The epoxy curing agent is characterized in that the synthesis formula comprises the following components in parts by weight: 10-80 parts of epoxy resin, 5-70 parts of organic phenol, 0.005-9 parts of catalyst, 5-60 parts of amine substance and 1-150 parts of solvent; the organic phenol is at least one selected from petroleum phenol, nonyl phenol and phenol; the catalyst is selected from at least one of dimethylethanolamine, N dimethylbenzylamine, potassium persulfate, triphenylphosphine and boron trifluoride; the preparation method of the epoxy curing agent comprises the following steps:
1) weighing epoxy resin, organic phenol and catalyst in the formula, adding into a reaction container, heating to 75-250 deg.C for maintaining
After the temperature is 0.5 to 7 hours, the temperature is reduced to 30 to 120 ℃, 1 to 75 parts of solvent is added to obtain an addition product of the epoxy resin and the organic phenol, and then the discharge is carried out; (2) adding amine substances and 1-60 parts of solvent in the formula into the reaction vessel, heating to 40-125 ℃, and reacting
Slowly adding the adduct of the epoxy resin and the organic phenol obtained in the step (1) under the stirring state, and preserving the heat for 0.4 to 6 hours at the temperature of between 70 and 135 ℃; (3) adding the rest solvent in the formula, and stirring for 5-100 minutes to obtain the epoxy curing agent.
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| CN201710257032.3A CN108727563B (en) | 2017-04-19 | 2017-04-19 | Epoxy curing agent |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1026188A2 (en) * | 1999-02-05 | 2000-08-09 | Kansai Paint Co., Ltd. | Resin composition for coating |
| CN101338018A (en) * | 2007-07-06 | 2009-01-07 | 上海树脂厂有限公司 | Epoxy curing agent and method for preparing same |
| CN103224612A (en) * | 2013-05-15 | 2013-07-31 | 程梦喜 | Solvent-free self-leveling epoxy resin curing agent and preparation method thereof |
| CN106046327A (en) * | 2016-06-28 | 2016-10-26 | 湖北绿色家园精细化工股份有限公司 | Epoxy prime coat curing agent prepared by modifying mixed amine system with benzyl benzoate leftovers and synthesis technique thereof |
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- 2017-04-19 CN CN201710257032.3A patent/CN108727563B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1026188A2 (en) * | 1999-02-05 | 2000-08-09 | Kansai Paint Co., Ltd. | Resin composition for coating |
| CN101338018A (en) * | 2007-07-06 | 2009-01-07 | 上海树脂厂有限公司 | Epoxy curing agent and method for preparing same |
| CN103224612A (en) * | 2013-05-15 | 2013-07-31 | 程梦喜 | Solvent-free self-leveling epoxy resin curing agent and preparation method thereof |
| CN106046327A (en) * | 2016-06-28 | 2016-10-26 | 湖北绿色家园精细化工股份有限公司 | Epoxy prime coat curing agent prepared by modifying mixed amine system with benzyl benzoate leftovers and synthesis technique thereof |
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