CN107254030B - A kind of acrylate ended aqueous epoxy curing agent and preparation method thereof having self-defoaming ability - Google Patents
A kind of acrylate ended aqueous epoxy curing agent and preparation method thereof having self-defoaming ability Download PDFInfo
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- CN107254030B CN107254030B CN201710507638.8A CN201710507638A CN107254030B CN 107254030 B CN107254030 B CN 107254030B CN 201710507638 A CN201710507638 A CN 201710507638A CN 107254030 B CN107254030 B CN 107254030B
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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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1494—Polycondensates modified by chemical after-treatment followed by a further chemical treatment thereof
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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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
- C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
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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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
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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
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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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- Polymers & Plastics (AREA)
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Abstract
The invention discloses a kind of acrylate ended aqueous epoxy curing agents for having self-defoaming ability, it is made of 10~20 parts of polyamine, 13.5~31 parts of epoxy resin, 6.5~19 parts of acrylate monomer and 30~70 parts of deionized water.The present invention, which first reacts polyamine with epoxy resin, is made epoxy-amine intermediate；Then acrylate monomer sealing end is added；Then unreacted small molecule and solvent is evaporated off, is eventually adding deionized water and obtains aqueous epoxy curing agent.The aqueous epoxy curing agent that the present invention is prepared significantly reduces while guaranteeing that curing agent has excellent compatibility with epoxy resin and mixes foam number and foam stabilizing time.
Description
Technical field
The present invention relates to technical field of coatings, and in particular to a kind of Water-borne modification oxygen resin curing agent and preparation method thereof.
Background technique
With the development of economy with social progress, the environmental consciousness of people gradually increased, and water paint has become existing
For the development trend of coatings industry.Aqueous epoxide resin paint has excellent physical and chemical performance, is widely used in anti-corrosion
The fields such as coating, industry ground slab coating, building coating, woodwork coating.Aqueous epoxide resin paint does dispersing agent with water, because of its tool
It is standby can in high humidity environment normal temperature cure and low volatilizable organic matter (VOC) and lesser peculiar smell etc. to the mankind and environment friend
Good feature and be concerned by people.
But aqueous epoxide resin paint causes it when forming a film because bubble is difficult to because it has amphipathic property simultaneously
It dissipates and limits application.
Summary of the invention
[technical problems to be solved]
Present invention aim to address above-mentioned prior art problems, provide a kind of acrylate envelope for having self-defoaming ability
Hold aqueous epoxy curing agent and preparation method thereof.
[technical solution]
In order to reach above-mentioned technical effect, the present invention takes following technical scheme:
A kind of acrylate ended aqueous epoxy curing agent having self-defoaming ability, it is by the substance of following mass parts
Composition:
10~20 parts of polyamine, 13.5~31 parts of epoxy resin, 6.5~19 parts of acrylate monomer and 30~70
The deionized water of part.
The further technical solution of the present invention, the acrylate monomer are methyl acrylate, ethyl acrylate, propylene
Acid butyl ester, benzyl acrylate, Hydroxyethyl Acrylate, hydroxypropyl acrylate, isobornyl acrylate, Isodecyl base
Ester, acrylic acid stearate, lauryl acid esters, acrylic acid card must ester, methyl methacrylate, ethyl methacrylate,
Propyl methacrylate, n-BMA, Isobutyl methacrylate, isobornyl methacrylate, metering system
Sour stearate, lauryl methacrylate, hydroxyethyl methacrylate, hydroxy propyl methacrylate, 2- Phenoxyethyl
One of acrylate, ethoxyethoxyethyl acrylate or a variety of mixtures.
A kind of acrylate ended aqueous epoxy curing agent preparation method described above having self-defoaming ability, it includes
Following steps:
(1) it is 55~80 DEG C of polyamine ethanol solution to temperature, epoxy resin ethanol solution, drop is added dropwise under stirring
After adding and keep thermotonus for a period of time after, obtain epoxy-amine intermediate；
(2) appropriate acrylate monomer is added into epoxy-amine intermediate, then stirring a period of time；
(3) distillation removal solvent and unreacted acrylate monomer；
(4) appropriate amount of deionized water is added and obtains aqueous epoxy curing agent.
The further technical solution of the present invention, in step (1), reaction a period of time refer to reaction 20~
30min。
The further technical solution of the present invention, in step (1), the polyamine ethanol solution refers to polyamine and second
Alcoholic solution presses the solution for waiting mass ratioes mixing；The epoxy resin ethanol solution refers to epoxy resin and ethanol solution according to quality
Than the solution being mixed to get for 4.9~10:1.
The further technical solution of the present invention, in step (1), the amount of the substance of the polyamine and epoxy resin it
Than for 2~2.1:1.
The further technical solution of the present invention, in step (2), the epoxy-amine intermediate and acrylate monomer
The ratio between the amount of substance be 1:2~2.1.
The further technical solution of the present invention, in step (2), the stirring be for a period of time controlled at 40~
100 DEG C of 2.5~3.5h of stirring.
It will be described in detail the present invention below.
It is 55~80 DEG C present invention defines the temperature of polyamine and epoxy resin hybrid reaction.Because of lower than 55 DEG C reactions
Speed is slow, and higher than 80 DEG C etoh solvent evaporation rates are too fast to be unfavorable for next step operation, while will increase gum deposit more than 80 DEG C
Risk.
The ratio between amount of epoxy-amine intermediate and acrylate monomer materials is 1:2~2.1.The temperature of the reaction should control
Within 40~100 DEG C, too low reaction temperature is unfavorable for reaction and carries out, and excessively high reaction temperature is volatilized same in accelerating alcohol
When will lead to acrylate monomer autohemagglutination.According to monomer difference and temperature difference, epoxy-amine intermediate is reacted with acrylate monomer
It is basically completed in 2.5h~3.5h, the increase reaction time will not bring other income, and the shortening time then will lead to monomer reaction
Not exclusively.
The additional amount of deionized water need to be suitably added according to the aqueous epoxy curing agent of required solid content or viscosity.
[beneficial effect]
Compared with prior art, the present invention have it is below the utility model has the advantages that
The present invention, as end-capping reagent, is guaranteeing curing agent and epoxy resin with excellent compatibility using acrylate monomer
While significantly reduce mixing foam number and foam stabilizing time.
Specific embodiment
Below with reference to the embodiment of the present invention, the invention will be further elaborated.
Embodiment 1:
1) triethylene tetramine ethanol solution is added into the reaction kettle equipped with condenser, thermometer, under 60 DEG C of stirring conditions
It is continuous that epoxy E-51 alcohol mixed solution is added dropwise, subsequent continuation of insurance temperature 20min is added dropwise and obtains epoxy-amine intermediate；It is described
Triethylene tetramine ethanol solution is mixed by the triethylene tetramine and 731.1g ethyl alcohol of 731.1g；The epoxy E-51 ethyl alcohol
Mixed solution is mixed by the ethanol solution of 924g epoxy E-51 and 92.4g.
2) 500g methyl methacrylate is added into epoxy-amine intermediate, 70 DEG C of constant temperature persistently stir 2.5h.
3) ethyl alcohol and unreacted small-molecule substance is distilled off.
4) addition 2155.1g deionized water obtains 50% solid content and obtains light yellow clear aqueous epoxy curing agent.
Embodiment 2
1) triethylene tetramine ethanol solution is added into the reaction kettle equipped with condenser, thermometer, under 70 DEG C of stirring conditions
It is continuous that epoxy E-44 ethanol solution is added dropwise, subsequent continuation of insurance temperature 20min is added dropwise and obtains epoxy-amine intermediate；The triethylene
Tetramine ethanol solution is mixed by the triethylene tetramine and 7.31g ethyl alcohol of 7.31g；The epoxy E-44 alcohol mixed solution
It is to be mixed by the ethanol solution of 11.2Kg epoxy E-44 and 2.24Kg.
2) 7.2Kg hydroxy propyl methacrylate is added into epoxy-amine intermediate, 60 DEG C of constant temperature persistently stir 3h.
3) ethyl alcohol and unreacted small-molecule substance is distilled off.
4) 17.14Kg deionized water is added and obtains the light yellow aqueous epoxy curing agent of 60% solid content.
Embodiment 3
1) epoxy E-51 is continuously added dropwise into the three-necked flask equipped with triethylene tetramine ethanol solution under 75 DEG C of stirring conditions
Ethanol solution is added dropwise subsequent continuation of insurance temperature 20min and obtains epoxy-amine intermediate；The triethylene tetramine ethanol solution be by
The triethylene tetramine and 146.23g ethyl alcohol of 146.23g mixes；The epoxy E-51 alcohol mixed solution is by 198g epoxy
The ethanol solution of E-44 and 20g mixes.
2) the addition 50g methyl methacrylate, 72.08g hydroxy propyl methacrylate into epoxy-amine intermediate, 60 DEG C
Constant temperature persistently stirs 3.5h.
3) ethyl alcohol and unreacted small-molecule substance is distilled off.
4) 669.47 deionized waters are added and obtain the light yellow clear aqueous epoxy curing agent of 40% solid content.
Embodiment 4
1) epoxy E-51 is continuously added dropwise into the three-necked flask equipped with triethylene tetramine ethanol solution under 75 DEG C of stirring conditions
Ethanol solution is added dropwise subsequent continuation of insurance temperature 20min and obtains epoxy-amine intermediate；The triethylene tetramine ethanol solution be by
The triethylene tetramine and 146.23g ethyl alcohol of 146.23g mixes；The epoxy E-51 alcohol mixed solution is by 198g epoxy
The ethanol solution of E-51 and 20g mixes.
2) 86g methyl acrylate is added into epoxy-amine intermediate, 50 DEG C of constant temperature persistently stir 3.5h.
3) ethyl alcohol and unreacted small-molecule substance is distilled off.
4) 645.35 deionized waters are added and obtain the light yellow clear aqueous epoxy curing agent of 40% solid content.
Embodiment 5
1) epoxy E-51 second is continuously added dropwise into the reaction kettle equipped with triethylene tetramine ethanol solution under 55 DEG C of stirring conditions
Alcoholic solution is added dropwise subsequent continuation of insurance temperature 30min and obtains epoxy-amine intermediate；The triethylene tetramine ethanol solution be by
The triethylene tetramine and 300g ethyl alcohol of 300g mixes；The epoxy E-51 alcohol mixed solution is by 406.2g epoxy E-51
It is mixed with the ethanol solution of 82g.
2) 238.22g hydroxy-ethyl acrylate is added into epoxy-amine intermediate, 70 DEG C of constant temperature persistently stir 2.5h.
3) ethyl alcohol and unreacted small-molecule substance is distilled off.
4) 944.42 deionized waters are added and obtain the light yellow clear aqueous epoxy curing agent of 50% solid content.
Embodiment 6
1) epoxy F-51 second is continuously added dropwise into the reaction kettle equipped with triethylene tetramine ethanol solution under 65 DEG C of stirring conditions
Alcoholic solution is added dropwise subsequent continuation of insurance temperature 20min and obtains epoxy-amine intermediate；The triethylene tetramine ethanol solution be by
The triethylene tetramine and 300g ethyl alcohol of 300g mixes；The epoxy F-51 alcohol mixed solution is by 406.2g epoxy F-51
It is mixed with the ethanol solution of 82g.
2) 68.38g ethyl acrylate, 68.38 methyl methacrylates, 130.14g first are added into epoxy-amine intermediate
Base hydroxy-ethyl acrylate, 60 DEG C of constant temperature persistently stir 3.5h.
3) ethyl alcohol and unreacted small-molecule substance is distilled off.
4) 973.1 deionized waters are added and obtain the light yellow clear aqueous epoxy curing agent of 50% solid content.
The aqueous epoxy curing agent that Examples 1 to 6 is prepared is (respectively with example 1, example 2, reality in following table 1
Example 3, example 4, example 5 and example 6 indicate) 0 with market part comparative sample 7,8,9 on sale according to the ratio with epoxy resin E-51 low speed
It is stirred 5min, the water of gross mass 100% is added, 40g lotion 2500r/min stirring 10min is taken to be placed in 100ml graduated cylinder
Observe bubbles volume.The results are shown in Table 1 for (applying 1) 0.
1 present invention of table applies 1 the ratio between foam number with market aqueous epoxy curing agent on sale
By curing agent prepared by example 1~6 and market part comparative sample 7,8,9 on sale according to the ratio with epoxy resin E-51
Mixing 5min is stirred at low speed, the water of total amount 50% is added, 40g lotion 2500r/min stirring 10min is taken to be placed on 100ml graduated cylinder
Middle observation bubbles volume.(applying 2) the results are shown in Table 2.
2 present invention of table applies 2 the ratio between foam number with market aqueous epoxy curing agent on sale
By curing agent prepared by example 1~6 and market part comparative sample 7,8,9 on sale according to the ratio with epoxy resin E-51
Stir at low speed mixing 5min, be added total amount 100% water, 20% 400 mesh calcium carbonate powders and total amount 1% BYK-333,
1% BYK-349, decompression row take 40ml lotion 2500r/min stirring 10min to be placed on view volume in 100ml graduated cylinder after steeping.
(applying 3) the results are shown in Table 3.
3 present invention of table applies 3 the ratio between foam number with market aqueous epoxy curing agent on sale
By curing agent prepared by example 1~6 and market part comparative sample 7,8,9 on sale according to the ratio with epoxy resin E-51
It stirs at low speed mixing 5min and lotion is made, be added after the water dilution of total amount 50% uniformly coated on room temperature curing on concrete substrate
7d is tested for the property, as a result such as table 4.
4 present invention of table and the ratio between the performance after the application of market aqueous epoxy curing agent on sale
The aqueous epoxy curing agent that the present invention is prepared, from table 1 it follows that 1~6 foam number 10 of 0min example~
12ml is far below 24~35ml of comparative sample 7~9；1~6 bubble of example has been completely severed disappearance after 30min, and comparative sample at this time
7~9 but still have 11~15ml foam stabilizing amount.From Table 2, it can be seen that 1~6 bubble of example after 30min under the conditions of large arch dam
It is completely severed disappearance, and comparative sample 7~9 still has 25~32ml foam stabilizing amount at this time and compared to 10min when is not significant
It reduces.From table 3 it is observed that example 1~6 can complete defoaming in 10min in the case where filler is added and is aided with auxiliary agent,
And comparative sample still has 4.5~5.5ml bubble cannot exclude after 30min.As can be seen from Table 4, example 1~6 and comparative sample 7
~9 in terms of traditional performance indifference.
In conclusion the aqueous epoxy curing agent that the present invention is prepared has well in guarantee curing agent and epoxy resin
Mixing foam number and foam stabilizing time are significantly reduced while compatibility.
Although reference be made herein to invention has been described for explanatory embodiment of the invention, and above-described embodiment is only this hair
Bright preferable embodiment, embodiment of the present invention are not limited by the above embodiments, it should be appreciated that those skilled in the art
Member can be designed that a lot of other modification and implementations, these modifications and implementations will fall in principle disclosed by the invention
Within scope and spirit.
Claims (8)
1. a kind of acrylate ended aqueous epoxy curing agent for having self-defoaming ability, it is characterised in that it is by following quality
The substance of part is made:
10~20 parts of polyamine, 13.5~31 parts of epoxy resin, 6.5~19 parts of acrylate monomer and 30~70 parts
Deionized water, preparation step are as follows:
(1) it is 55~80 DEG C of polyamine ethanol solution to temperature, epoxy resin ethanol solution is added dropwise under stirring, drips
Finish after and keep thermotonus for a period of time after, obtain epoxy-amine intermediate；
(2) appropriate acrylate monomer is added into epoxy-amine intermediate, then stirring a period of time；
(3) distillation removal solvent and unreacted acrylate monomer；
(4) appropriate amount of deionized water is added and obtains aqueous epoxy curing agent.
2. the acrylate ended aqueous epoxy curing agent according to claim 1 for having self-defoaming ability, feature exist
In the acrylate monomer be methyl acrylate, ethyl acrylate, butyl acrylate, benzyl acrylate, dihydroxypropyl second
Ester, hydroxypropyl acrylate, isobornyl acrylate, Isodecyl base ester, stearyl acrylate acid esters, lauryl acid
The positive fourth of ester, acrylic acid card must ester, methyl methacrylate, ethyl methacrylate, propyl methacrylate, methacrylic acid
Ester, Isobutyl methacrylate, isobornyl methacrylate, stearyl methacrylate, lauryl methacrylate,
Hydroxyethyl methacrylate, hydroxy propyl methacrylate, 2- phenoxyethyl acrylate, ethoxyethoxyethyl acrylic acid
One of ester or a variety of mixtures.
3. a kind of acrylate ended aqueous epoxy curing agent preparation side of any of claims 1 or 2 for having self-defoaming ability
Method, it is characterised in that it the following steps are included:
(1) it is 55~80 DEG C of polyamine ethanol solution to temperature, epoxy resin ethanol solution is added dropwise under stirring, drips
Finish after and keep thermotonus for a period of time after, obtain epoxy-amine intermediate；
(2) appropriate acrylate monomer is added into epoxy-amine intermediate, then stirring a period of time；
(3) distillation removal solvent and unreacted acrylate monomer；
(4) appropriate amount of deionized water is added and obtains aqueous epoxy curing agent.
4. the acrylate ended aqueous epoxy curing agent preparation method according to claim 3 for having self-defoaming ability,
It is characterized in that described reaction a period of time refers to 20~30min of reaction in step (1).
5. the acrylate ended aqueous epoxy curing agent preparation method according to claim 3 for having self-defoaming ability,
It is characterized in that the polyamine ethanol solution refers to what polyamine was mixed with ethanol solution by equal mass ratioes in step (1)
Solution；The epoxy resin ethanol solution refers to that epoxy resin and ethanol solution are mixed to get according to mass ratio for 4.9~10:1
Solution.
6. the acrylate ended aqueous epoxy curing agent preparation method according to claim 3 for having self-defoaming ability,
It is characterized in that the ratio between amount of substance of the polyamine and epoxy resin is 2~2.1:1 in step (1).
7. the acrylate ended aqueous epoxy curing agent preparation method according to claim 3 for having self-defoaming ability,
It is characterized in that in step (2), the ratio between amount of substance of the epoxy-amine intermediate and acrylate monomer be 1:2~
2.1。
8. the acrylate ended aqueous epoxy curing agent preparation method according to claim 3 for having self-defoaming ability,
It is characterized in that the stirring is controlled at 40~100 DEG C of 2.5~3.5h of stirring for a period of time in step (2).
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| CN201710507638.8A CN107254030B (en) | 2017-06-28 | 2017-06-28 | A kind of acrylate ended aqueous epoxy curing agent and preparation method thereof having self-defoaming ability |
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| TW201915081A (en) * | 2017-09-29 | 2019-04-16 | 台灣日邦樹脂股份有限公司 | Epoxy resin composition, Cured product and Formulation for curing agent |
| CN112225879B (en) * | 2020-10-19 | 2023-03-10 | 南昌航空大学 | Modified amine curing agent and preparation method thereof |
| CN112662277A (en) * | 2020-12-24 | 2021-04-16 | 绵阳惠利环氧工程有限公司 | Exterior wall putty modified epoxy resin primer and application method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104558529A (en) * | 2014-12-26 | 2015-04-29 | 江苏苏博特新材料股份有限公司 | Preparation method of amide self-emulsifying water-borne epoxy resin curing agent |
| CN106280277A (en) * | 2016-08-12 | 2017-01-04 | 中国电建集团西北勘测设计研究院有限公司 | A kind of preparation method and application of environmental protection low viscosity high-strength epoxy radicals grouting material |
| EP3173395A1 (en) * | 2015-11-24 | 2017-05-31 | Dresdner Lackfabrik novatic GmbH Co. KG | Coating system for concrete surfaces |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104558529A (en) * | 2014-12-26 | 2015-04-29 | 江苏苏博特新材料股份有限公司 | Preparation method of amide self-emulsifying water-borne epoxy resin curing agent |
| EP3173395A1 (en) * | 2015-11-24 | 2017-05-31 | Dresdner Lackfabrik novatic GmbH Co. KG | Coating system for concrete surfaces |
| CN106280277A (en) * | 2016-08-12 | 2017-01-04 | 中国电建集团西北勘测设计研究院有限公司 | A kind of preparation method and application of environmental protection low viscosity high-strength epoxy radicals grouting material |
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