CN106554482A - A kind of preparation method of the star-like aqueous epoxy curing agent of high-performance - Google Patents
A kind of preparation method of the star-like aqueous epoxy curing agent of high-performance Download PDFInfo
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- CN106554482A CN106554482A CN201611055834.8A CN201611055834A CN106554482A CN 106554482 A CN106554482 A CN 106554482A CN 201611055834 A CN201611055834 A CN 201611055834A CN 106554482 A CN106554482 A CN 106554482A
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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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
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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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Abstract
The invention discloses a kind of preparation method of the star-like aqueous epoxy curing agent of high-performance, including：(1) basic amine is preheated to into 40～80 DEG C, adds diglycidyl ether and bisphenol A type epoxy resin to carry out chain extension, react 2～3h, obtain basic amine chain extension thing A；(2) polyetheramine is preheated to into 40～80 DEG C, adds diglycidyl ether and bisphenol A type epoxy resin to carry out chain extension, react 2～3h, obtain polyetheramine chain extension thing B；(3) A is mixed with B and is preheated to 50～90 DEG C, add polyfunctional epoxy resin, react 2～5h, chain extension thing is connected on polyfunctional epoxy resin and forms hub-and-spoke configuration；(4) blocked after 50～90 DEG C of addition mono-epoxy compounds, reacts 2～3h；(5) finally temperature adjustment is to 40～60 DEG C and adds deionized water that the aqueous epoxy curing agent that solid content is 30%～70% is obtained.The aqueous epoxy curing agent of the prepared hub-and-spoke configuration of the present invention, with excellent mobility, and can preferably wrap epoxy resin during epoxy resin mixing and emulsifying, film has excellent combination property.
Description
Technical field
The present invention relates to technical field of coatings, more particularly to a kind of preparation side of the star-like aqueous epoxy curing agent of high-performance
Method.
Background technology
Epoxy resin has excellent mechanical performance, adhesive property, decay resistance, is widely used in paint field.Pass
Contain many solvents in the solvent epoxy varnish of system, very big harm, therefore water-base epoxy are generated to environment and health of human body
Resin arises at the historic moment and instead of solvent epoxy varnish in many applications, greatly reduces environmental pollution.Water-base epoxy tree
The emulsion system of fat be different from solvent epoxy varnish homogeneous system, the former state of cure often not as good as the latter, before causing
The partial properties of person are slightly inferior to the latter, but aqueous epoxy resins are entirely capable of suitable for the use under non-critical conditions.It is aqueous at present
The developing direction of epoxy resin is mainly resin Water-borne modification and curing agent Water-borne modification, and wherein curing agent Water-borne modification can more improve solidification
Physical performance and reduction environmental pollution, have a extensive future.
Aqueous epoxy curing agent need first to take into account water solubility, reactivity and and epoxy resin compatibility, secondly need and
The intensity of solidfied material, toughness, corrosion resistance etc. are turned round and look at, the synthesis of obtained aqueous epoxy curing agent in presently commercially available or patent
Performance cannot fully meet the requirement of practical application.A kind of aqueous epoxy curing agent is disclosed in patent CN101613460A
Preparation method：First chain extending reaction is carried out with epoxy long-chain compound and polyethylene polyamine, then add asphalt mixtures modified by epoxy resin toward chain extension thing
Fat dilution reacts, and is eventually adding deionized water and obtains product.Hydrophilic component in aqueous epoxy curing agent obtained in this method
Polyethylene polyamine content is too high, causes hydrophily larger and not good with epoxy resin compatibility, causes state of cure not high, solidifies
Physical performance is poor.A kind of aqueous epoxy curing agent of good hydrophilic property is disclosed in patent CN105801869A：Polyethers and ring are used first
Oxygen resin reaction obtains addition compound product, then which is obtained polyethers-epoxy-amide adduct with m-phenylene diamine (MPD) reaction, finally uses phenyl
The mixture end-blocking of glycidol ether and benzyl glycidyl ether.Pfpe molecule amount used by this aqueous epoxy curing agent compared with
Greatly, although the toughness of water-soluble and solidfied material is preferably but reactivity reduces too many, cause the development of solidfied material properties very slow,
Solidification is also incomplete.A kind of Diamond Search aqueous epoxy curing agent is disclosed in patent CN103788343A, the method for preparation is：First
110～160 DEG C of reactions during polyetheramine is added dropwise to epoxy resin and epoxy terminated glycidol ether generate intermediate, then centre
React during body is added drop-wise to aminated compounds and at 60～90 DEG C, be eventually adding deionized water and product is obtained.The method first step
Middle epoxy is excessive relative to polyetheramine and reaction temperature is very high, is easily caused gel, and reaction is difficult control, and product quality is difficult
Ensure.
So, the aqueous epoxy curing agent that be obtained to make the combination property of film fully meet application request was both needed
From suitable raw material and proportioning, the reaction process condition that need to be easily controlled again.
The content of the invention
Present invention aims to a current industry difficult problem, there is provided a kind of system of the star-like aqueous epoxy curing agent of high-performance
Preparation Method.The preparation method process is simple of the present invention, reaction condition are gentle, and products therefrom is in hub-and-spoke configuration, with excellent stream
Dynamic property, good with epoxy resin compatibility, film has excellent combination property.
The technical solution adopted in the present invention is：
A kind of preparation method of the star-like aqueous epoxy curing agent of high-performance, comprises the steps：(1) basic amine is preheated to
40～80 DEG C, the mixture for being charged with diglycidyl ether and bisphenol A type epoxy resin carries out chain extension, and isothermal reaction 2～
3h, obtains basic amine chain extension thing A；(2) polyetheramine is preheated to into 40～80 DEG C, is charged with diglycidyl ether and bisphenol-A
The mixture of type epoxy resin carries out chain extension, and 2～3h of isothermal reaction obtains polyetheramine chain extension thing B；(3) A is mixed with B and pre-
Heat is charged with polyfunctional epoxy resin to 50～90 DEG C, and 2～5h of isothermal reaction, chain extension thing are connected on polyfunctional epoxy resin
Upper formation hub-and-spoke configuration；(4) reaction completes to add mono-epoxy compounds to be blocked after 50～90 DEG C, 2～3h of isothermal reaction；
(5) after the completion of reacting, temperature adjustment is to 40～60 DEG C and adds deionized water to dilute, and obtains the water that solid content is 30%～70%
Property epoxy hardener.
Further, the mass fraction of each component is：Basic amine 2%～20%；Polyetheramine 5%～30%；Two shrink
Glycerin ether 5%～20%；Bisphenol A type epoxy resin 3%～15%；Polyfunctional epoxy resin 2%～15%；Mono-epoxy compounds
1%～10%；Deionized water 30%～70%.
Further, the basic amine be ethylenediamine, hexamethylene diamine, diethylenetriamine, triethylene tetramine, TEPA, five
Hexamine, m-phenylene diamine (MPD), m-xylene diamine, IPD,One or more mixtures in alkane diamines.
Further, the diglycidyl ether is ethylene glycol diglycidylether, propylene glycol diglycidylether, butanediol
In diglycidyl ether, season neopentyl glycol diglycidyl glycerin ether, polyethyleneglycol diglycidylether, polypropylene glycol diglycidyl ether
One or more mixtures.
Further, the bisphenol A type epoxy resin is mixed for one or more in E-54, E-51, E-44, E-20, E-12
Compound.
Further, the polyetheramine is the production of HUNTSMAN companiesED600、ED900、ED2003、
One or more mixtures in D230, D400, D2000.
Further, the polyfunctional epoxy resin be resorcinol formaldehyde epoxy resin, 1,1,2,2- tetra- (para hydroxybenzene
Base) four tetraglycidel ether epoxy resin of ethane, triphenol methylmethane triglycidyl ether epoxy resin, 1,3,5-trihydroxybenzene three-glycidyl
One or more mixtures in ether epoxy resin.
Further, the mono-epoxy compounds is butyl glycidyl ether, allyl glycidyl ether, C12～C14 alkyl
One or more mixtures in glycidol ether, phenyl glycidyl ether, benzyl glycidyl ether.
The invention has the beneficial effects as follows：
(1) aqueous epoxy curing agent is prepared using basic amine and polyetheramine, with it is simple using basic amine compared with amine content and
Active hydrogen content is reduced, still have it is certain it is water miscible under the premise of lipophile slightly improve, therefore carry with the compatibility of epoxy resin
Height, working life extend, and the intensity of epoxy curing compound, toughness and corrosion resistance are improved.
(2) chain extension, one side mixture are carried out using the mixture of diglycidyl ether and bisphenol A type epoxy resin to amine
Can guarantee that the intensity and toughness of epoxy curing compound, another aspect diglycidyl ether serve as bisphenol A type epoxy resin diluent and
It is easy to be added dropwise, by solvent need not be added, reduces reaction system viscosity, diglycidyl ether participates in reaction without the need for removing in addition.
(3) aqueous epoxy curing agent of hub-and-spoke configuration is obtained with polyfunctional epoxy resin as skeleton, compared with linear structure,
Possess more side chains, so having more preferable mobility, and can preferably be embedded in during epoxy resin mixing and emulsifying and wrap up
Firmly epoxy resin, it is difficult because stirring departs from into water, so as to the content of the curing agent that reduces dissociating in water, improve epoxy resin and solid
The probability that agent is contacted and reacted, and then improve the combination property of epoxy resin cured product.
(4) bisphenol A-type and polyfunctional epoxy resin are introduced in aqueous epoxy curing agent preparation process, is on the one hand strengthened and ring
The compatibility of oxygen tree fat, on the other hand improves the intensity and corrosion resistance of epoxy curing compound.
(5) aqueous epoxy curing agent viscosity can be reduced using mono-epoxy compounds end-blocking, extends working life.
(6) preparation method process is simple, reaction condition are gentle.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, below in conjunction with skill of the embodiment to the present invention
Art scheme carries out complete description, it is clear that described embodiment is a part of embodiment of the invention, rather than the enforcement of whole
Example.Based on the embodiment in the present invention, what those of ordinary skill in the art were obtained under the premise of creative work is not made
Every other embodiment, belongs to the scope of protection of the invention.
21.0g ethylenediamines are heated to 80 DEG C by embodiment 1 (1), are charged with 21.0g polypropylene glycol diglycidyl ethers
Chain extension is carried out with the mixture of 13.4g E-20, isothermal reaction 2h obtains ethylenediamine chain extension thing A；(2) by 101.6g polyetheramines
D400 is heated to 80 DEG C, and the mixture for being charged with 21.0g polypropylene glycol diglycidyl ethers and 15.6g E-20 is expanded
Chain, isothermal reaction 2h obtain polyetheramine D400 chain extension thing B；(3) A is mixed with B and is preheated to 80 DEG C, be charged with 11.4g
Resorcinol formaldehyde epoxy resin, isothermal reaction 3h, chain extension thing are connected on resorcinol formaldehyde epoxy resin and form hub-and-spoke configuration；
(4) reaction completes to add 20.0g phenyl glycidyl ethers to be blocked after 80 DEG C, isothermal reaction 2h；(5) temperature after the completion of reacting
Degree is adjusted to 60 DEG C and adds 337.5g deionized waters to dilute, and obtains the aqueous epoxy curing agent that solid content is 40%.
It is 1 that obtained aqueous epoxy curing agent is pressed active hydrogen with epoxy radicals mol ratio with E-51:1 mixing and emulsifying is prepared and is applied
Film, conserves one week after measuring stability and tests film performance according to standard GB/T 22374-2008, as a result as shown in table 1.
50.9g diethylenetriamines are heated to 50 DEG C by embodiment 2 (1), are charged with 31.3g season neopentyl glycol diglycidyls sweet
The mixture of oily ether and 24.3g E-51 carries out chain extension, and isothermal reaction 2.5h obtains diethylenetriamine chain extension thing A；(2) will
99.0g polyetheramine ED900 are heated to 55 DEG C, are charged with 22.7g season neopentyl glycol diglycidyl glycerin ethers and 16.2g E-51
Mixture carries out chain extension, and isothermal reaction 2.5h obtains polyetheramine ED900 chain extension thing B；(3) A is mixed with B and is preheated to 75 DEG C,
Four tetraglycidel ether epoxy resin of 32.7g 1,1,2,2- tetra- (p-hydroxybenzene) ethane is charged with, isothermal reaction 3h expands
Chain thing is connected on 1,1,2,2- tetra- (p-hydroxybenzene) ethane, four tetraglycidel ether epoxy resin and forms hub-and-spoke configuration；(4) react
Complete to add 15.1g C12～C14 alkyl glycidyl ethers to be blocked after 70 DEG C, isothermal reaction 2h；(5) after the completion of reacting
Temperature adjustment is to 50 DEG C and adds 292.2g deionized waters to dilute, and obtains the aqueous epoxy curing agent that solid content is 50.0%.
It is 1 that obtained aqueous epoxy curing agent is pressed active hydrogen with epoxy radicals mol ratio with E-51:1 mixing and emulsifying is prepared and is applied
Film, conserves one week after measuring stability and tests film performance according to standard GB/T 22374-2008, as a result as shown in table 1.
67.1g m-phenylene diamine (MPD)s are heated to 75 DEG C by embodiment 3 (1), are charged with 22.7g polyethylene glycol diglycidyls
The mixture of ether and 30.1g E-54 carries out chain extension, and isothermal reaction 3h obtains m-phenylene diamine (MPD) chain extension thing A；(2) by 50.6g polyethers
Amine D230 is heated to 80 DEG C, and the mixture for being charged with 21.8g polyethyleneglycol diglycidylethers and 20.2g E-54 is carried out
Chain extension, isothermal reaction 3h obtain polyetheramine D230 chain extension thing B；(3) A is mixed with B and is preheated to 75 DEG C, be charged with
46.3g 1,3,5-trihydroxybenzene triglycidyl ether epoxy resin, isothermal reaction 3h, chain extension thing are connected on 1,3,5-trihydroxybenzene three-glycidyl ether ring
Hub-and-spoke configuration is formed on oxygen tree fat；(4) reaction completes to add 31.2g butyl glycidyl ethers to be blocked after 75 DEG C, constant temperature
Reaction 3h；(5) after the completion of reacting, temperature adjustment is to 40 DEG C and adds 210.0g deionized waters to dilute, and obtains solid content for 58.0%
Aqueous epoxy curing agent.
It is 1 that obtained aqueous epoxy curing agent is pressed active hydrogen with epoxy radicals mol ratio with E-51:1 mixing and emulsifying is prepared and is applied
Film, conserves one week after measuring stability and tests film performance according to standard GB/T 22374-2008, as a result as shown in table 1.
93.5g IPDs are heated to 60 DEG C by embodiment 4 (1), are charged with 45.2g ethylene glycol two and are shunk sweet
The mixture of oily ether and 22.6g E-44 carries out chain extension, and isothermal reaction 3h obtains IPD chain extension thing A；(2) will
128.0g polyetheramine ED2003 are heated to 75 DEG C, are charged with the mixed of 3.5g ethylene glycol diglycidylethers and 4.6g E-44
Compound carries out chain extension, and isothermal reaction 3h obtains polyetheramine ED2003 chain extension thing B；(3) A is mixed with B and is preheated to 85 DEG C, it is past
35.3g triphenol methylmethane triglycidyl ether epoxy resin is added wherein, isothermal reaction 4h, chain extension thing are connected on triphenol methylmethane three
Hub-and-spoke configuration is formed on tetraglycidel ether epoxy resin；(4) reaction completes to add 25.1g benzyl glycidyl ethers to enter after 75 DEG C
Row end-blocking, isothermal reaction 2h；(5) after the completion of reacting, temperature adjustment is to 55 DEG C and adds 192.7g deionized waters to dilute, consolidate
Content is 65.0% aqueous epoxy curing agent.
It is 1 that obtained aqueous epoxy curing agent is pressed active hydrogen with epoxy radicals mol ratio with E-51:1 mixing and emulsifying is prepared and is applied
Film, conserves one week after measuring stability and tests film performance according to standard GB/T 22374-2008, as a result as shown in table 1.
81.6g m-xylene diamines are heated to 70 DEG C by embodiment 5 (1), are charged with 30.3g butanediol 2-glycidyls
The mixture of ether and 17.4g E-54 carries out chain extension, and isothermal reaction 3h obtains m-xylene diamine chain extension thing A；(2) 92.0g is gathered
Ether amines D2000 are heated to 75 DEG C, and the mixture for being charged with 10.1g butanediol diglycidyl ethers and 6.5g E-54 is carried out
Chain extension, isothermal reaction 3h obtain polyetheramine D2000 chain extension thing B；(3) A is mixed with B and is preheated to 90 DEG C, be charged with
27.8g 1,3,5-trihydroxybenzene triglycidyl ether epoxy resin, isothermal reaction 5h, chain extension thing are connected on 1,3,5-trihydroxybenzene three-glycidyl ether ring
Hub-and-spoke configuration is formed on oxygen tree fat；(4) reaction completes to add 11.4g allyl glycidyl ethers to be blocked after 85 DEG C, permanent
Temperature reaction 2.5h；(5) after the completion of reacting, temperature adjustment is to 45 DEG C and adds 338.7g deionized waters to dilute, and obtaining solid content is
45.0% aqueous epoxy curing agent.
It is 1 that obtained aqueous epoxy curing agent is pressed active hydrogen with epoxy radicals mol ratio with E-51:1 mixing and emulsifying is prepared and is applied
Film, conserves one week after measuring stability and tests film performance according to standard GB/T 22374-2008, as a result as shown in table 1.
1 film performance of table
As shown in Table 1, the ability of aqueous epoxy curing agent emulsion epoxy resin obtained in the present invention is strong, multiple with epoxy resin
With obtained aqueous epoxy resins film good stability, excellent combination property, standard requirement is complied fully with.
Finally it should be noted that：Various embodiments above only to illustrate technical scheme, rather than a limitation；To the greatest extent
Pipe has been described in detail to the present invention with reference to foregoing embodiments, it will be understood by those within the art that：Its according to
So the technical scheme described in foregoing embodiments can be modified, or which part or all technical characteristic are entered
Row equivalent；And these modifications or replacement, do not make the essence of appropriate technical solution depart from various embodiments of the present invention technology
The scope of scheme.
Claims (8)
1. the preparation method of the star-like aqueous epoxy curing agent of a kind of high-performance, it is characterised in that comprise the steps：(1) by basis
Amine is preheated to 40～80 DEG C, and the mixture for being charged with diglycidyl ether and bisphenol A type epoxy resin carries out chain extension, constant temperature
2～3h of reaction, obtains basic amine chain extension thing A；(2) polyetheramine is preheated to into 40～80 DEG C, is charged with diglycidyl ether
Chain extension is carried out with the mixture of bisphenol A type epoxy resin, 2～3h of isothermal reaction obtains polyetheramine chain extension thing B；(3) A is mixed with B
Merging is preheated to 50～90 DEG C, is charged with polyfunctional epoxy resin, and 2～5h of isothermal reaction, chain extension thing are connected on multifunctional ring
Hub-and-spoke configuration is formed on oxygen tree fat；(4) reaction completes to add mono-epoxy compounds to be blocked after 50～90 DEG C, isothermal reaction
2～3h；(5) after the completion of reacting, temperature adjustment is to 40～60 DEG C and adds deionized water to dilute, obtain solid content for 30%～
70% aqueous epoxy curing agent.
2. the preparation method of the star-like aqueous epoxy curing agent of high-performance according to claim 1, it is characterised in that described each
The mass fraction of component is：Basic amine 2%～20%；Polyetheramine 5%～30%；Diglycidyl ether 5%～20%；Bisphenol-A
Type epoxy resin 3%～15%；Polyfunctional epoxy resin 2%～15%；Mono-epoxy compounds 1%～10%；Deionized water
30%～70%.
3. the preparation method of the star-like aqueous epoxy curing agent of high-performance according to claim 1, it is characterised in that the base
Plinth amine is ethylenediamine, hexamethylene diamine, diethylenetriamine, triethylene tetramine, TEPA, pentaethylene hexamine, m-phenylene diamine (MPD), isophthalic
Dimethylamine, IPD,One or more mixtures in alkane diamines.
4. the preparation method of the star-like aqueous epoxy curing agent of high-performance according to claim 1, it is characterised in that described two
Glycidol ether is ethylene glycol diglycidylether, propylene glycol diglycidylether, butanediol diglycidyl ether, season pentanediol
One or more mixtures in diglycidyl ether, polyethyleneglycol diglycidylether, polypropylene glycol diglycidyl ether.
5. the preparation method of the star-like aqueous epoxy curing agent of high-performance according to claim 1, it is characterised in that described double
Phenol A types epoxy resin is one or more mixtures in E-54, E-51, E-44, E-20, E-12.
6. the preparation method of the star-like aqueous epoxy curing agent of high-performance according to claim 1, it is characterised in that described poly-
Ether amines are the production of HUNTSMAN companiesIn ED600, ED900, ED2003, D230, D400, D2000 one
Plant or several mixtures.
7. the preparation method of the star-like aqueous epoxy curing agent of high-performance according to claim 1, it is characterised in that described many
Functional epoxy resins be resorcinol formaldehyde epoxy resin, 1,1,2,2- tetra- (p-hydroxybenzene) ethane, four diglycidyl ether epoxy
Resin, triphenol methylmethane triglycidyl ether epoxy resin, the one kind or several in 1,3,5-trihydroxybenzene triglycidyl ether epoxy resin
Plant mixture.
8. the preparation method of the star-like aqueous epoxy curing agent of high-performance according to claim 1, it is characterised in that the list
Epoxide is that butyl glycidyl ether, allyl glycidyl ether, C12～C14 alkyl glycidyl ethers, phenyl glycidyl are sweet
One or more mixtures in oily ether, benzyl glycidyl ether.
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| CN110156957A (en) * | 2019-05-29 | 2019-08-23 | 上海骁鹏新材料科技有限公司 | Aqueous epoxy curing agent and its preparation method and application |
| CN114591492A (en) * | 2020-12-07 | 2022-06-07 | 万华化学集团股份有限公司 | Water-based epoxy curing agent and preparation method and application thereof |
| CN114605616A (en) * | 2020-12-03 | 2022-06-10 | 万华化学集团股份有限公司 | Quick-drying nonionic waterborne epoxy curing agent and preparation method and application thereof |
| CN114991730A (en) * | 2022-06-13 | 2022-09-02 | 中海石油(中国)有限公司 | Thick oil thermal recovery simulation interlayer and manufacturing method thereof |
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| CN114605616A (en) * | 2020-12-03 | 2022-06-10 | 万华化学集团股份有限公司 | Quick-drying nonionic waterborne epoxy curing agent and preparation method and application thereof |
| CN114605616B (en) * | 2020-12-03 | 2023-05-26 | 万华化学集团股份有限公司 | Quick-drying nonionic water-based epoxy curing agent, and preparation method and application thereof |
| CN114591492A (en) * | 2020-12-07 | 2022-06-07 | 万华化学集团股份有限公司 | Water-based epoxy curing agent and preparation method and application thereof |
| CN114591492B (en) * | 2020-12-07 | 2023-05-30 | 万华化学集团股份有限公司 | Water-based epoxy curing agent and preparation method and application thereof |
| CN114991730A (en) * | 2022-06-13 | 2022-09-02 | 中海石油(中国)有限公司 | Thick oil thermal recovery simulation interlayer and manufacturing method thereof |
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