CN114349935A - Low-viscosity water-based epoxy curing agent and preparation method thereof - Google Patents
Low-viscosity water-based epoxy curing agent and preparation method thereof Download PDFInfo
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- CN114349935A CN114349935A CN202210030310.2A CN202210030310A CN114349935A CN 114349935 A CN114349935 A CN 114349935A CN 202210030310 A CN202210030310 A CN 202210030310A CN 114349935 A CN114349935 A CN 114349935A
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- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 37
- 239000004593 Epoxy Substances 0.000 title claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 29
- 229920000570 polyether Polymers 0.000 claims abstract description 29
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 13
- 239000012153 distilled water Substances 0.000 claims abstract description 11
- 229920000768 polyamine Polymers 0.000 claims abstract description 11
- 239000002994 raw material Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 6
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003141 primary amines Chemical class 0.000 claims description 4
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 claims description 2
- KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-UHFFFAOYSA-N 0.000 claims description 2
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 claims description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 2
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 239000004848 polyfunctional curative Substances 0.000 claims 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 239000003822 epoxy resin Substances 0.000 abstract description 6
- 229920000647 polyepoxide Polymers 0.000 abstract description 6
- 239000000839 emulsion Substances 0.000 abstract description 5
- 229920005989 resin Polymers 0.000 abstract description 4
- 239000011347 resin Substances 0.000 abstract description 4
- 238000005265 energy consumption Methods 0.000 abstract description 2
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 abstract description 2
- 238000004904 shortening Methods 0.000 abstract description 2
- 239000007787 solid Substances 0.000 description 7
- 229920006334 epoxy coating Polymers 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 229960001124 trientine Drugs 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000012855 volatile organic compound Substances 0.000 description 2
- 239000004970 Chain extender Substances 0.000 description 1
- 241001391944 Commicarpus scandens Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
Classifications
-
- 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
- C08G59/50—Amines
- C08G59/5006—Amines aliphatic
-
- 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
- C08G59/50—Amines
- C08G59/5006—Amines aliphatic
- C08G59/5013—Amines aliphatic containing more than seven carbon atoms, e.g. fatty amines
-
- 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
- C08G59/50—Amines
- C08G59/5026—Amines cycloaliphatic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
Abstract
The invention discloses a low-viscosity water-based epoxy curing agent and a preparation method thereof, wherein the curing agent is prepared from the following raw materials in parts by weight: 7-16 parts of polyether amine, 5-10 parts of polyether monoamine, 7-12 parts of polyamine, 21-30 parts of ethylene glycol diglycidyl ether and 45-50 parts of distilled water. The invention can complete the chain extension and end capping process of the curing agent only by one-step synthesis reaction, simplifies the synthesis steps, thereby shortening the synthesis time of the curing agent and reducing the energy consumption, and the prepared low-viscosity waterborne epoxy curing agent can be mixed with liquid epoxy resin or epoxy resin emulsion to be used in various occasions requiring high resin content.
Description
Technical Field
The invention relates to the technical field of epoxy coatings, and particularly relates to a low-viscosity water-based epoxy curing agent and a preparation method thereof.
Background
Epoxy resin is a thermosetting polymer material with good bonding, electrical insulation, corrosion resistance, high strength and other properties, and the water-based epoxy coating mainly takes water as a dispersing agent, so that the water-based epoxy coating has the characteristics of being capable of being constructed on a wet base surface and in a high-humidity environment, and being low in Volatile Organic Compounds (VOC), low in peculiar smell and the like, and is friendly to human and environment, and people pay attention to the water-based epoxy coating. In general, waterborne epoxy curing agents require the incorporation of epoxy resin segments in the molecular segments to achieve good compatibility with the resin, but the incorporation of epoxy segments rapidly increases the viscosity of the curing agent. In order to reduce the viscosity, a method of adding a cosolvent and reducing the solid content of the curing agent is generally adopted, the cosolvent is contrary to the development direction of the environmental protection of the waterborne epoxy, and the reduction of the solid content of the curing agent greatly limits the application range of the waterborne epoxy system.
At present, some researches are carried out on the low-viscosity water-based epoxy curing agent in China. For example, patent CN113527118A realizes the technology of preparing low-viscosity waterborne epoxy curing by one-step synthesis, but in order to ensure proper active hydrogen equivalent and hydrophilicity, the curing agent still contains a large amount of-NH2The primary amine affects the compatibility of the epoxy resin, and particularly, the epoxy resin aqueous emulsion is very unstable after being mixed and is very easy to break emulsion. Patent CN1637039A adopts a method of compounding with a hydrophilic stable waterborne epoxy curing agent of a finished product to provide enough emulsion stability to solve the problem of synthesized-NH2The problem of stability of primary amine is the concept of one-step synthesis and one-step compounding, and the actual effect of the obtained curing agent is influenced by the compounded finished curing agent. CN109369906A provides a solution for preparing a low-viscosity aqueous epoxy curing agent from maleic anhydride modified polyetheramine, and the use of the solution in the aspects of fast curing and deep curing is limited because only polyetheramine and a single maleic anhydride chain extender can be selected as raw materials. The synthesis of low-viscosity aqueous epoxy curing agents represented by patents CN110511356A, CN110746578A and CN111333818A requires multiple steps of epoxy-amine adduct preparation, prepolymer preparation and end-capping reaction, and the process is complicated and takes too long, which is not suitable for mass production.
Disclosure of Invention
In order to solve the technical problems, the invention provides a low-viscosity waterborne epoxy curing agent and a preparation method thereof, the viscosity of the low-viscosity waterborne epoxy curing agent prepared according to the scheme is not higher than 500mPa & s under the condition of 55% solid content, and the low-viscosity waterborne epoxy curing agent is particularly suitable for preparing normal-temperature curing epoxy coating needing high solid content and low viscosity.
In order to achieve the technical effects, the invention provides the following technical scheme:
the low-viscosity water-based epoxy curing agent is prepared from the following raw materials in parts by weight: 7-16 parts of polyether amine, 5-10 parts of polyether monoamine, 7-12 parts of polyamine, 21-30 parts of ethylene glycol diglycidyl ether and 45-50 parts of distilled water.
According to a further technical scheme, the polyether amine is selected from one or more of D230, D400, HK-511 and ED-600 of HUNTSMAN.
The further technical scheme is that the polyamine is selected from one or more of diethylenetriamine, triethylene tetramine, isophorone diamine, menthane diamine, 3 '-dimethyl-4, 4' -diaminodicyclohexyl methane, 1, 3-bis (aminomethyl) cyclohexane, m-xylylenediamine, diethyl toluene diamine and amino ethyl piperazine.
The further technical proposal is that the ethylene glycol diglycidyl ether contains epoxy group mole number and-NH2The mole ratio of the primary amine is 1.00 to 1.05: 1.
The further technical scheme is that the polyether monoamine accords with the following structural characteristics:
wherein R is H or CH3The value of x is 19-41, and the value of y is 3-10.
The invention also provides a preparation method of the low-viscosity water-based epoxy curing agent, which comprises the following steps: (1) uniformly mixing polyether amine, polyether monoamine and polyamine with the formula ratio in an ethanol solution, continuously dropwise adding ethylene glycol diglycidyl ether at 65-70 ℃, and keeping the temperature for 0.5-1 h to obtain a first solution; (2) distilling the first solution to 120 ℃ and recovering the solvent to obtain a second solution; (3) and adding distilled water into the second solution at the temperature of 40-55 ℃ to obtain the low-viscosity waterborne epoxy curing agent.
Compared with the prior art, the invention has the following beneficial effects: the invention adopts low-viscosity difunctional glycidyl ether to carry out continuous chain extension reaction on a polyamine mixture containing polyether amine to prepare the low-viscosity waterborne epoxy curing agent which can be mixed with liquid epoxy resin or epoxy resin emulsion to be used in various occasions requiring high resin content. The invention can complete the chain extension and end capping processes of the curing agent only by one-step synthesis reaction, thereby simplifying the synthesis steps, shortening the synthesis time of the curing agent and reducing the energy consumption.
Detailed Description
The invention will be further explained and illustrated with reference to specific examples.
Example 1
The raw materials comprise: polyether amine D23013.8 parts, polyether monoamine M20705.2 parts, isophorone diamine IPDA 7.6 parts, triethylene tetramine TETA 4.4 parts, ethylene glycol diglycidyl ether 24 parts and distilled water 45 parts, wherein M2070 is polyether monoamine of a Henschel advanced material.
The preparation method comprises the following steps: (1) uniformly mixing polyether amine, polyether monoamine and polyamine with the formula ratio in an ethanol solution, continuously dropwise adding ethylene glycol diglycidyl ether at 65-70 ℃, and keeping the temperature for 0.5h to obtain a first solution; (2) distilling the first solution to 120 ℃ and recovering the solvent to obtain a second solution; (3) and (3) cooling to 40 ℃, and then adding distilled water into the second solution to dilute the second solution until the solid content is 55%, so as to obtain the low-viscosity waterborne epoxy curing agent.
Example 2
The raw materials comprise: polyether amine D23013 parts, polyether monoamine M10007 parts, isophorone diamine IPDA 6.7 parts, triethylene tetramine TETA 5.1 parts, ethylene glycol diglycidyl ether 23.2 parts, and distilled water 45 parts, wherein M1000 is polyether monoamine of Henscman advanced material.
The preparation method comprises the following steps: (1) uniformly mixing polyether amine, polyether monoamine and polyamine with the formula ratio in an ethanol solution, continuously dropwise adding ethylene glycol diglycidyl ether at 65-70 ℃, and keeping the temperature for 0.5h to obtain a first solution; (2) distilling the first solution to 120 ℃ and recovering the solvent to obtain a second solution; (3) and (3) cooling to 55 ℃, and then adding distilled water into the second solution to dilute the second solution until the solid content is 55%, so as to obtain the low-viscosity waterborne epoxy curing agent.
Example 3
The raw materials comprise: polyether amine D4009.6 parts, polyether monoamine M20708.9 parts, diethylenetriamine DETA 9.9 parts, ethylene glycol diglycidyl ether 21.6 parts and distilled water 50 parts, wherein M2070 is polyether monoamine of a Henschel advanced material.
The preparation method comprises the following steps: (1) uniformly mixing polyether amine, polyether monoamine and polyamine in a formula amount in an ethanol solution, continuously dropwise adding ethylene glycol diglycidyl ether at 65-70 ℃, and preserving heat for 1h to obtain a first solution; (2) distilling the first solution to 120 ℃ and recovering the solvent to obtain a second solution; (3) and (3) cooling to 50 ℃, and then adding distilled water into the second solution to dilute until the solid content is 50%, so as to obtain the low-viscosity waterborne epoxy curing agent.
Performance testing
The examples 1-3 and the reference curing agent were separately mixed with HEXION's EPIKOTETM3510-W-60 resins were blended and tested for viscosity, the results of which are shown in Table 1.
TABLE 1
As shown in Table 1, the low-viscosity waterborne epoxy curing agents prepared in examples 1-3 all have significantly lower viscosity at 25 ℃ than similar waterborne epoxy curing agents in the market. Wherein Anquamine721, Aradur 3985, 62.5% Aradur 36 are commercially available curing agents.
Although the present invention has been described herein with reference to the illustrated embodiments thereof, which are intended to be preferred embodiments of the present invention, it is to be understood that the invention is not limited thereto, and that numerous other modifications and embodiments can be devised by those skilled in the art that will fall within the spirit and scope of the principles of this disclosure.
Claims (6)
1. The low-viscosity water-based epoxy curing agent is characterized by being prepared from the following raw materials in parts by weight: 7-16 parts of polyether amine, 5-10 parts of polyether monoamine, 7-12 parts of polyamine, 21-30 parts of ethylene glycol diglycidyl ether and 45-50 parts of distilled water.
2. The low viscosity aqueous epoxy hardener as claimed in claim 1, wherein the polyetheramine is selected from one or more of D230, D400, HK-511, ED-600 of HUNTSMAN.
3. The low viscosity aqueous epoxy hardener as claimed in claim 1, wherein the polyamine is selected from one or more of diethylenetriamine, triethylenetetramine, isophoronediamine, menthanediamine, 3 '-dimethyl-4, 4' -diaminodicyclohexylmethane, 1, 3-bis (aminomethyl) cyclohexane, m-xylylenediamine, diethyltoluenediamine, aminoethylpiperazine.
4. The low viscosity aqueous epoxy hardener as claimed in claim 1, wherein the ethylene glycol diglycidyl ether contains epoxy groups in a molar ratio of-NH2The mole ratio of the primary amine is 1.00 to 1.05: 1.
5. A low viscosity aqueous epoxy hardener as claimed in claim 1, characterized in that the polyether monoamine complies with the following structural features:
wherein R is H or CH3The value of x is 19-41, and the value of y is 3-10.
6. A method for preparing the low viscosity aqueous epoxy hardener as claimed in any one of claims 1 to 5, comprising the steps of: (1) uniformly mixing polyether amine, polyether monoamine and polyamine with the formula ratio in an ethanol solution, continuously dropwise adding ethylene glycol diglycidyl ether at 65-70 ℃, and keeping the temperature for 0.5-1 h to obtain a first solution; (2) distilling the first solution to 120 ℃ and recovering the solvent to obtain a second solution; (3) and adding distilled water into the second solution at the temperature of 40-55 ℃ to obtain the low-viscosity waterborne epoxy curing agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210030310.2A CN114349935B (en) | 2022-01-12 | 2022-01-12 | Low-viscosity aqueous epoxy curing agent and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202210030310.2A CN114349935B (en) | 2022-01-12 | 2022-01-12 | Low-viscosity aqueous epoxy curing agent and preparation method thereof |
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| Publication Number | Publication Date |
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| CN114349935A true CN114349935A (en) | 2022-04-15 |
| CN114349935B CN114349935B (en) | 2024-05-31 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202210030310.2A Active CN114349935B (en) | 2022-01-12 | 2022-01-12 | Low-viscosity aqueous epoxy curing agent and preparation method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115073713A (en) * | 2022-07-22 | 2022-09-20 | 安徽衡光新材料科技有限公司 | Waterborne toughening epoxy curing agent, preparation method and waterborne epoxy composition prepared from waterborne toughening epoxy curing agent |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5032629A (en) * | 1989-03-13 | 1991-07-16 | Rutgerswerke Ag | Epoxy hardening agents |
| US5489630A (en) * | 1994-11-28 | 1996-02-06 | Air Products And Chemicals, Inc. | Self-emulsifying epoxy curing agent |
| US20020072575A1 (en) * | 2000-03-23 | 2002-06-13 | Bakelite Ag | Curing agents for expoxide compounds, method for their production and use of same |
| US20070292620A1 (en) * | 2004-07-09 | 2007-12-20 | Huntsman Advanced Materials Americas Inc. | Amine Compositions |
| CN105026455A (en) * | 2013-03-01 | 2015-11-04 | Sika技术股份公司 | Composition and method of making water borne epoxy hardener for use in two-component epoxy self levelling compounds with long pot life, fast cure and low shrinkage characteristics |
| CN105593264A (en) * | 2013-09-30 | 2016-05-18 | 气体产品与化学公司 | Epoxy liquid curing agent compositions |
| WO2018212766A1 (en) * | 2017-05-16 | 2018-11-22 | Evonik Degussa Gmbh | Epoxy curing agents, compositions and uses thereof |
| CN109370384A (en) * | 2018-10-30 | 2019-02-22 | 绵阳惠利环氧工程有限公司 | A kind of preparation method of self-emulsifying type non-ionic water epoxy hardener |
| CN109923145A (en) * | 2017-02-06 | 2019-06-21 | 亨斯迈石油化学有限责任公司 | Curing agent for epoxy resin |
-
2022
- 2022-01-12 CN CN202210030310.2A patent/CN114349935B/en active Active
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5032629A (en) * | 1989-03-13 | 1991-07-16 | Rutgerswerke Ag | Epoxy hardening agents |
| US5489630A (en) * | 1994-11-28 | 1996-02-06 | Air Products And Chemicals, Inc. | Self-emulsifying epoxy curing agent |
| US20020072575A1 (en) * | 2000-03-23 | 2002-06-13 | Bakelite Ag | Curing agents for expoxide compounds, method for their production and use of same |
| US20070292620A1 (en) * | 2004-07-09 | 2007-12-20 | Huntsman Advanced Materials Americas Inc. | Amine Compositions |
| CN105026455A (en) * | 2013-03-01 | 2015-11-04 | Sika技术股份公司 | Composition and method of making water borne epoxy hardener for use in two-component epoxy self levelling compounds with long pot life, fast cure and low shrinkage characteristics |
| CN105593264A (en) * | 2013-09-30 | 2016-05-18 | 气体产品与化学公司 | Epoxy liquid curing agent compositions |
| CN109923145A (en) * | 2017-02-06 | 2019-06-21 | 亨斯迈石油化学有限责任公司 | Curing agent for epoxy resin |
| WO2018212766A1 (en) * | 2017-05-16 | 2018-11-22 | Evonik Degussa Gmbh | Epoxy curing agents, compositions and uses thereof |
| CN109370384A (en) * | 2018-10-30 | 2019-02-22 | 绵阳惠利环氧工程有限公司 | A kind of preparation method of self-emulsifying type non-ionic water epoxy hardener |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115073713A (en) * | 2022-07-22 | 2022-09-20 | 安徽衡光新材料科技有限公司 | Waterborne toughening epoxy curing agent, preparation method and waterborne epoxy composition prepared from waterborne toughening epoxy curing agent |
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| CN114349935B (en) | 2024-05-31 |
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