CN103224608A - Heat-curable epoxy-amine anti-seepage sealant - Google Patents
Heat-curable epoxy-amine anti-seepage sealant Download PDFInfo
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- CN103224608A CN103224608A CN 201310096501 CN201310096501A CN103224608A CN 103224608 A CN103224608 A CN 103224608A CN 201310096501 CN201310096501 CN 201310096501 CN 201310096501 A CN201310096501 A CN 201310096501A CN 103224608 A CN103224608 A CN 103224608A
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- 0 NCCNCC*CCNCCN Chemical compound NCCNCC*CCNCCN 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N CC(C)(C1)CC(C)(CN)CC1N Chemical compound CC(C)(C1)CC(C)(CN)CC1N RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N NCCCCCCN Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- UGXBEFDZRYGNEA-UHFFFAOYSA-N NCCNCCCNCCNCCNCCN Chemical compound NCCNCCCNCCNCCNCCN UGXBEFDZRYGNEA-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N NCCNCCN Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention relates to a heat-curable epoxy-amine anti-seepage sealant. The heat-curable epoxy-amine anti-seepage sealant is an anti-seepage composition containing a resin or a resin/filler system, and still has a good anti-seepage performance during low-temperature curing The composition comprises an aromatic compound having an m-substituted epoxy functionality, a multifunctional aliphatic amine, one or a plurality of optional fillers, one or a plurality of optional adhesion promoters, and an optional phenolic curing accelerator.
Description
The application divides an application, and the applying date of original application is that March 30, application number in 2006 are that 200680054025.3 (PCT/US2006/012657), denomination of invention are " hot curable epoxy-amine anti-seepage fluid sealant ".
According to the MDA972-93-2-0014 agreement that ARL (Army Research Laboratories) is issued, the present invention carries out under the support of United States Government.Government has certain right to the present invention.
Technical field
The present invention relates to be used for electronics and opto-electronic device anti-seepage sealant, tackiness agent, encapsulants and coating (such as this specification sheets and claims use, tackiness agent, seal gum, encapsulants and coating are similar materials, all have the nature and function of tackiness agent, seal gum and coating.When any one is narrated, other also be believed to comprise interior.）
Background technology
The polymer impervious material is widely used in a lot of packings and the security application, for example food, beverage, pharmaceuticals, makeup, agricultural-food, electronic component, casting, pipeline and tubulation.As permeability-reducing admixture; the exchange of the permeable molecule between their restriction environment and the protected system; therefore and the local flavor or the fragrance of food or cosmetic composition have been preserved; stop the corrosion of moisture or oxygen, and protection automobile instrument panel element surface avoids by normally used solvent infiltration in coating or the priming paint to electronic component.Because different systems need have different barrier performances, therefore good permeability-reducing admixture in a certain application may be considered to the bad permeability-reducing admixture of effect in another kind is used.
Description of drawings
Fig. 1 is the sub-device of peripheral sealed photoelectric.Fig. 2 contains and does not contain the epoxy/TEPA(amine of catalyzer isothermal cure under 75 ℃) the differential scanning calorimetry coverage diagram of adulterant.
Summary of the invention
The present invention is the antiseepage composition that comprises resin or resin/filler systems, and it can solidify at low temperatures and still keeps simultaneously outstanding barrier performance.This composition comprises: the aromatic compound of the epoxy functionalities that the position replaces between (a) having, and (b) multifunctional aliphatic amine, (c) randomly, one or more fillers, (d) randomly, one or more adhesionpromoters, and (e) randomly, the phenols curing catalyst.
This antiseepage composition can use separately or use with other curable resin and various filler combination.The composition that obtains shows commercial acceptable solidification rate, high crosslink density and good adhesive property, therefore makes it can be effective to seal and encapsulate various goods, particularly electronics, photoelectron and MEMS device.
In another embodiment, the present invention is a low-temperature curable antiseepage composition, it comprises the aromatic ring oxygen compound, and this aromatic ring oxygen compound is selected from: the fusible resol of epoxidation, bisphenol-f diglycidylether, bisphenol-A diglycidylether, bis-phenol-E diglycidylether, epoxidation phenol novolac resin, epoxidation cresols novolac resin, encircle the halide derivative of Resins, epoxy, naphthalene diglycidylether and these materials more; Polyfunctional amine; And optional phenols curing catalyst.
Detailed Description Of The Invention
The present invention is the thermofixation anti-seepage sealant, comprises: the aromatic compound of the epoxy functionalities that the position replaces between (a) having and (b) multifunctional aliphatic amine.This antiseepage tackiness agent or seal gum randomly comprise (c) one or more fillers, (d) one or more adhesionpromoters.
R
1, R
2, R
3, R
4Be selected from: hydrogen, halogen, cyano group, alkyl, aryl and the substituted alkyl or the aryl that can contain epoxy functionalities; R
5And R
6Be to have formula-C
nH
2n-divalence hydrocarbon connection portion, wherein n=0-4(when n is 0, R
5And R
6Do not exist); Wherein, R
1, R
2, R
3, R
4, R
5And R
6In any two parts that can form same ring texture;
L
1, L
2, L
3, L
4, L
5, L
6Be direct key or the divalent linker that is selected from following radicals:
EP and EP ' are the curable epoxy functionality, are selected from: aliphatic epoxy, glycidyl ether, cycloaliphatic epoxy.
The example of epoxide group includes but not limited to:
Wherein these structural hydrogen can be replaced by one or more alkyl or halogen group.
The exemplary aromatic compound of the epoxy functionalities that the position replaces between having includes but not limited to:
For satisfying various performance requirements, can use one or more other Resins, epoxy, and these resins are preferably selected from: bisphenol-f diglycidylether, novolac glycidyl ethers, encircle epoxy, naphthalene diglycidylether and halogenated glycidyl ethers more.
In this manual, the multifunctional aliphatic amine of term is meant the amine that has in the following groups at least two in same molecule:
Wherein R ' and R ' ' are independently selected from hydrogen, alkyl or substituted alkyl.R ' " is hydrogen or divalent alkyl/substituted alkyl linking group.The multifunctional aliphatic amine that is fit to includes but are not limited to those that are selected from following radicals:
As used in this specification sheets and claims, the word curing catalyst refers to identical notion with catalyzer.Suitable promotor is difunctionality or multifunctional phenolic compound.The phenolic compound that is fit to includes but not limited to: 2,4, and the 6-tri(dimethylaminomethyl)phenol, Resorcinol, the 4-ethyl resorcinol, 2,5-dimethyl Resorcinol, Phloroglucinol, 2-nitro Phloroglucinol, 5-methoxyl group Resorcinol, the 5-methyl isophthalic acid, the 3-dihydroxy-benzene, the 2-methylresorcinol, 4-bromine Resorcinol, the 4-chloro resorcinol, 4,6-two chloro resorcinols, 3,5-dihydroxyl-phenyl aldehyde, 2,4-dihydroxyl-phenyl aldehyde, 3, the 5-methyl dihydroxy benzoate, 2, the 4-methyl dihydroxy benzoate, 1,2,4-benzene triol, pyrogallol, 3, the 5-dihydroxybenzyl alcohol, 2', the 6'-resacetophenone, 2', the 4'-resacetophenone, 3', the 5'-resacetophenone, 2', 4'-dihydroxyl-Propiophenone, 2', 4'-dihydroxyl-3'-methyl acetophenone, 2,4,5-trihydroxy--phenyl aldehyde, 2,3, the 4-tri hydroxybenzaldehyde, 2,4, the 6-tri hydroxybenzaldehyde, 3, the 5-resorcylic acid, 2, the 4-resorcylic acid, 2, the 6-resorcylic acid, the 2-nitro-resorcinol, 1, the 3-dihydroxy naphthlene, quinhydrones, toluhydroquinone, 2, the 3-dimethyl hydroquinone, 2-methoxyl group quinhydrones, chlorohydroquinone, 2', the 5'-resacetophenone, 2-sec.-propyl-1, the 4-Benzenediol, 2, the 5-resorcylic acid, 2,3-dicyano Resorcinol, 1, the 4-dihydroxy naphthlene, 2', 5'-dihydroxy phenyl ethyl ketone, 1-(2,5-dihydroxyl-4-aminomethyl phenyl) ethyl ketone, Tert. Butyl Hydroquinone, 2, the 5-methyl dihydroxy benzoate, (2, the 5-dihydroxy phenyl) acetate, 2,4, the 5-trihydroxybenzoic acid, 4,7-dihydroxyl-3-methyl isophthalic acid-indone, 2,5-two chlorohydroquinones, tetrafluoro-Resorcinol, 2, the 5-dihydric ethyl benzoate, 2-(2,5-dihydroxy-benzene methylene radical) propane dinitrile, 2-bromo-1, the 4-Benzenediol, (2, the 5-dihydroxy phenyl) ethyl acetate, 1-(2,4,5-trihydroxy-phenyl)-1-butanone, 2,5-dihydroxyl-4-methoxyl methyl benzoate, 2,6-dinitrobenzene-1,4-Benzenediol, 2,4,5-trihydroxy-phenyl L-Ala, (2, the 5-dihydroxy phenyl)-(phenyl) ketone, 2,5-di-t-butyl-1, the 4-Benzenediol, 2-(6-methylheptyl)-1, the 4-Benzenediol, 2-(1,1,3, the 3-tetramethyl butyl)-1, the 4-Benzenediol, 2,5-dihydroxyl terephthalic acid dimethyl ester, 2,4,5-three chloro-3,6-dihydroxy phenyl cyanogen, 2,5-two tert-pentyls-1,4-Benzenediol, 2,5-two bromo-1, the 4-Benzenediol, 2,4-diethyl-3,6-dihydroxyl-phosphenylic acid dimethyl ester, pyrocatechol, 2,3-naphthalene glycol, the 5-methyl isophthalic acid, 2,3-benzene triol, the 4-methyl pyrocatechol, the 3-methyl pyrocatechol, the 3-fluoro pyrocatechol, 3-methoxyl group pyrocatechol, 4-chlorine pyrocatechol, 4,5-dichloro pyrocatechol, the 4-tert-butyl catechol, 3,4,5,6-tetrachloro-1,2-Benzenediol, 3-sec.-propyl-6-methyl pyrocatechol, the 3-tertiary butyl-6-methyl pyrocatechol, 3,4-dihydroxy phenyl cyanogen, 3,5-di-t-butyl pyrocatechol, 3,5-di-isopropyl pyrocatechol, 3, the 4-Dihydroxy benzaldehyde, 4-(1,1,3, the 3-tetramethyl butyl)-1, the 2-Benzenediol, 4-(1, the 2-dihydroxy ethyl)-1, the 2-Benzenediol, 1-(3, the 4-dihydroxy phenyl) ethyl ketone, 3, the 4-resorcylic acid, 3,4,5-trihydroxybenzene methane amide, 4-nitro-1, the 2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-1, the 2-Benzenediol, 5-methyl-3-(1,1,3, the 3-tetramethyl butyl)-1, the 2-Benzenediol, (3, the 4-dihydroxy phenyl) acetate, 2-(3,4-dihydroxy-benzene methylene radical) propane dinitrile, 3,5-dinitrobenzene-1,2-Benzenediol, 3, the 4-methyl dihydroxy benzoate, 2-chloro-1-(3, the 4-dihydroxy phenyl) ethyl ketone, phenyl (2,3,4-trihydroxy-phenyl) ketone, 3,4,5-trihydroxybenzoic acid isopropyl ester, 3,4-dihydroxyl-2-aminomethyl phenyl L-Ala, 3-bromo-4, the 5-resorcylic acid, 2-(3,4-dihydroxyl-5-anisole methylene radical) propane dinitrile, 3-(3, the 4-dihydroxy phenyl) ethyl propionate, 2-phenyl-1-(2,3,4-trihydroxy--phenyl) ethyl ketone and 3,4,5-trihydroxy--N-(2-hydroxyethyl) benzamide.
The filler that is fit to includes but not limited to: silica powder, fused silica, amorphous silica, talcum, granulated glass sphere, graphite, carbon black, aluminum oxide, clay and nanoclay, mica, vermiculite, aluminium nitride and boron nitride.Additional suitable filler comprises metal-powder and tinsel, for example: silver, copper, gold, tin, tin/lead alloy and other alloy.Organic filler powder for example poly-(zellon), poly-(chlorotrifluoroethylene) and poly-(vinylidene chloride) also can use.Also can utilize the filler with siccative or oxygen scavenqer effect, it includes but not limited to: CaO, BaO, Na
2SO
4, CaSO
4, MgSO
4, zeolite, silica gel, P
2O
5, CaCl
2And Al
2O
3
The composition of epoxy-amine system can be pre-mixed, or is kept in the independent container and uses the equipment as static mixer to mix at the scene.Also can be pre-mixed the part composition, for example, sub-fraction epoxy composition is joined in the amine and make amine oligomer/prepolymer.The amount of epoxy should enough be lacked, and does not take place thereby there is pectisation.Then this mixture is further mixed with remaining epoxy component.Alternatively, also can be before application with one or more components dissolved in one or more solvents.
Can realize the application of these formulations by using various technologies, it includes but not limited to: syringe dispensing, silk screen printing, stencilization, spraying, roller coat, ink jet printing, spin coating, dip-coating, vacuum-evaporation and similar technology.Goods are depended in the selection of application method, and in such expertise that is chosen in those skilled in the art.
Embodiment
The epoxy-amine adulterant of embodiment 1. various ratios
Present embodiment has illustrated the stoichiometric importance of epoxy-amine in the thermofixation adulterant.Bisphenol-f diglycidylether (deriving from Hexion Specialty Chemicals) and Triethylenetetramine (TETA) (TETA with Epoxy Research Resin RSL-1739, Aldrich) or tetren (TEPA, mixture ACROS) is in table 1(TETA sample) and show the 2(TEPA sample) shown in various ratios mix.The all samples of listing in these tables all comprises the siloxane surface additive B YK-310 of 0.2wt%.All in vacuum chamber, outgas after every kind of sample mix, and on sheet glass, solidified 100 minutes at 100 ℃.At the permeability coefficient of under 50 ℃, 100%RH, measuring solidified sample on the Mocon Permeatran3/33.As shown in these tables, calculate mol ratio and the epoxide group and the epoxide group when of amine nitrogen and the ratio of amine hydrogen of epoxy and amine molecule.For TETA(table 1) in, when the ratio of epoxide group and amine hydrogen is about 1:1, obtain the minimum moisture permeable coefficient in 3.4 to 3.7 gram square feet skies, mil/100.This ratio is confirmed as best proportion.When higher epoxy content, it is more crisp that film becomes, and under disruptive situation with it from the difficulty more that do not becoming of taking off on glass.Than high amine content the time, it is soft more that film becomes, and can't fully solidify.The sample (table 2) that contains TEPA and RSL-1739 has identical tendency.Minimum moisture permeable coefficient is 3.6 to 4.0 gram square feet skies, mil/100, and it obtains during for 1:1 in epoxide group and amine hydrogen ratio equally.
Table 1.RSL-1739/TETA formulation
Table 2.RSL-1739/TEPA formulation
Embodiment 2. contains the formulation of various epoxies
Present embodiment has illustrated the influence of epoxy construction to penetrating quality.The formulation that preparation TEPA and other epoxy or epoxy make up, described epoxy comprises: ERL-4221(Dow Chemical), resorcinol diglycidyl ether (deriving from CVC Specialty Chemicals) and Epiclon EXA-835LV(Danippon Ink and Chemicals Co. with ERISYS RDGE).Formulation and infiltration thereof the results are shown in the table 3.Unless indicate in addition in table 3, all formulations all prepare as defoamer with epoxide group and the amine hydrogen ratio of 1:1 and the BYK-310 that contains 0.2wt%, and make it 100 ℃ of curing 100 minutes on sheet glass.The formulation that comprises cycloaliphatic epoxy ERL-4221 does not fully solidify.Independent RDGE formulation and all have result preferably with the RDGE formulation of other glycidyl epoxy adulterant form has hyposmosis coefficient (2.0 to 2.5 gram square feet sky, mil/100).
The permeability coefficient of the various Resins, epoxy of table 3. solidified under 100 ℃/100min/TEPA adulterant
Example 3. contains the formulation of various amine
Present embodiment has illustrated the influence of the structure of amine to the water vapour permeability of different cured epoxies/amine adulterant.Use 80/20RDGE/835LV to select, several adulterants are studied as epoxy.As shown in the following Table 4, the amine with multiple skeleton structure is all tested, and wherein the ratio of epoxide group and amine hydrogen is 1:1.All samples all solidified 100 minutes down at 100 ℃.Containing tetren just like TEPA(), the TETA(Triethylenetetramine (TETA)) or the DETA(diethylenetriamine) the system of multifunctional aliphatic amine in observe lower water vapour permeability.It is as shown in the table, aromatic amine/epoxy systems or do not melt or do not solidify.
Table 4. is in the epoxy/amine system that contains 80/20RDGE/835LV epoxy adulterant, and amine structure changes the influence to water vapour permeability
Embodiment 4. solidifies under different condition
Present embodiment has illustrated that phenol catalyst influences epoxy-amine system solidified.The TEPA of 0.37g is joined in the bottle of the settled solution that contains 1.32g RDGE and 0.33g Epiclon EXA-835LV.Whole mixt was mixed one minute with vortex mixer.Carry out isothermal cure research immediately on Perkin Elmer DSC under 75 ℃ and 100 ℃, the result is summarised in the table 5.
The table 5. epoxy/isothermal cure of TEPA adulterant under differing temps
It is as shown in the table, when not using catalyzer, solidifies the obviously longer time 75 ℃ of following curing ratio down at 100 ℃.This is by reaching the peak value heat release and need the longer time and 90% the required time of curing of finishing being confirmed.Another sample is prepared as follows: the 0.082g Resorcinol is mixed 1.32g RDGE and 0.33g Epiclon EXA-835LV(based on epoxy, the Resorcinol of 5wt%) mixture in, 100 ℃ down heating 10 minutes to make clear soln.Behind the cool to room temperature, add 0.37g TEPA, and use the vortex mixer mixing solutions.And study the isothermal cure of this formulation once more.This catalytic formulation has had tangible improvement on curing performance.With do not compared by catalytic sample, the time that reaches the time of peak temperature and reach total heat release value of 90% all is shortened.The film that solidified 20 minutes at 75 ℃ of following catalyst-frees is a viscosity, but when adding catalyzer, film is noncohesive and anti-scratching.
Embodiment 5. phenol load the influence to curing properties
Present embodiment shows that phenol catalyst loads the influence for curing properties.Be similar to embodiment 4 preparation samples, on Perkin Elmer DSC, be heated to 150 ℃, analyze with 10 ℃/min.All formulations are that 1:1 is prepared with the ratio of epoxide group and amine hydrogen all.The results are shown in the table 6.Do not contain dihydroxyphenyl propane or only contain the sample of 1.5% to 5% dihydroxyphenyl propane, begin to solidify at about 65 ℃.When the content of dihydroxyphenyl propane increases to 10%, be solidificated under about 55 ℃ lower temperature and begin.Along with the increase that dihydroxyphenyl propane loads, cure peak temperature reduces.
The various dihydroxyphenyl propanes of table 6. load the curing of epoxy/TETA adulterant down
Embodiment 6. different phenol catalysis epoxies/amine solidified relatively
Present embodiment has been showed the influence of phenol catalyst to curing properties and curing back water vapour permeability.Several epoxy-TETA samples that comprise different phenol catalysts have been contrasted.In this case, the mixture of preparation 6.64g RDGE, 1.67g Epiclon835LV and 1.67g TETA by be heated to 150 ℃ with 10 ℃/min on Perkin Elmer DSC, obtains solidification value and heat release information (Δ H is in J/g).As shown in this embodiment, Resorcinol can reduce solidification value and obtain and 100 ℃ of suitable penetrating qualities of uncatalyzed sample of solidifying 100 minutes down.This permeation data is collected under 50 ℃ and 100%RH.Under the situation of bisphenol-A, observe the obvious increase of infiltration.Another kind of phenol, 2-hydroxyl-4-methoxyl group benzophenone (HMBP) does not have help to solidifying at all.
The comparison of the phenol curing catalyst of table 7. epoxy-TETA adulterant (wt% is based on epoxy)
The Resorcinol curing catalysts of embodiment 7. various replacements
The Resorcinol form of several replacements is screened under 5wt%, to determine whether solidification value can further reduce.Shown in following table 8, all Resorcinol analogues all reduce cure peak temperature, but do not compare not obviously improvement with Resorcinol itself.
Table 8.(80/20RDGE/835LV)/TEPA in the hot DSC of replacement resorcinol compound of 5wt%
The two component formulations that embodiment 8. fills
With micron order silica and pyrogenic silica rheology modifier, prepare two silica filled component epoxy-amine systems.Its one-tenth is respectively in the table 9.
Table 9. liang component is filled epoxy-amine system
Epoxy and Resorcinol are heated to 110 ℃ with the dissolving Resorcinol.After the cooling, add the silane adhesionpromoter, use vortex mixer sample mix.Add filler and rheology modifier then, and, outgas afterwards and spend the night with three roller runner milling biased samples.TEPA is added to the epoxy systems of filling and uses wooden stick and vortex mixer thorough mixing.
By about 1/4th inches two adhesive tapes (～5 mil) of administration interval on the aluminium sheet that applies at TEFLON, tested for adhesion energy.Use scraping blade, formulation is pulled into film between adhesive tape.The glass-chip of a slice slide glass and several 4 * 4 millimeters is wiped clean with Virahol and in Virahol, soaked 24 hours.From Virahol, remove this slide glass and chip and air-dry, carry out 5 minutes UV ozone clean subsequently.Then chip is placed in the film of formulation and pats to drench entire chip.From the formulation coating, take out this chip and be placed on the slide glass.Pat chip so that formulation soaks between chip and slide glass.This seal gum formulation was solidified 20 minutes in 75-80 ℃ baking box.Use is equipped with the shear adhesion of the Royce Instrument552100K detection solidified sample of 100Kg pressure head and 300 mil die tools (die tool).Find this dry adhesion power more than 40Kg, and under a week and fortnight 65 ℃ and 80%RH, behind the hydrothermal aging, still can keep this level.
The moisture vapor transmission coefficient of finding above-mentioned formulation is 1.1 gram square inch skies, mil/100.This permeation data is collected under 50 ℃ and 100%RH.
Claims (3)
1. curable antiseepage composition, it comprises:
(a) aromatic ring oxygen compound, it is selected from: resorcinol diglycidyl ether, bisphenol-f diglycidylether, bisphenol-A diglycidylether, bis-phenol-E diglycidylether, epoxidation phenol novolac resin, epoxidation cresols novolac resin, epoxidation can dissolve resol, encircle Resins, epoxy more, the halide derivative of naphthalene diglycidylether and these materials;
(b) multifunctional aliphatic amine, it is selected from:
(c) randomly, one or more fillers,
(d) randomly, one or more adhesionpromoters,
(e) randomly, phenols curing catalyst.
2. curable antiseepage composition according to claim 1, wherein, described phenols curing catalyst exists and is selected from: 2,4, the 6-tri(dimethylaminomethyl)phenol, Resorcinol, the 4-ethyl resorcinol, 2,5-dimethyl Resorcinol, Phloroglucinol, 2-nitro Phloroglucinol, 5-methoxyl group Resorcinol, the 5-methyl isophthalic acid, the 3-dihydroxy-benzene, the 2-methylresorcinol, 4-bromine Resorcinol, the 4-chloro resorcinol, 4,6-two chloro resorcinols, 3,5-dihydroxyl-phenyl aldehyde, 2,4-dihydroxyl-phenyl aldehyde, 3, the 5-methyl dihydroxy benzoate, 2, the 4-methyl dihydroxy benzoate, 1,2,4-benzene triol, pyrogallol, 3, the 5-dihydroxybenzyl alcohol, 2', the 6'-resacetophenone, 2', the 4'-resacetophenone, 3', the 5'-resacetophenone, 2', 4'-dihydroxyl-Propiophenone, 2', 4'-dihydroxyl-3'-methyl acetophenone, 2,4,5-trihydroxy--phenyl aldehyde, 2,3, the 4-tri hydroxybenzaldehyde, 2,4, the 6-tri hydroxybenzaldehyde, 3, the 5-resorcylic acid, 2, the 4-resorcylic acid, 2, the 6-resorcylic acid, the 2-nitro-resorcinol, 1, the 3-dihydroxy naphthlene, quinhydrones, toluhydroquinone, 2, the 3-dimethyl hydroquinone, 2-methoxyl group quinhydrones, chlorohydroquinone, 2', the 5'-resacetophenone, 2-sec.-propyl-1, the 4-Benzenediol, 2, the 5-resorcylic acid, 2,3-dicyano Resorcinol, 1, the 4-dihydroxy naphthlene, 2', 5'-dihydroxy phenyl ethyl ketone, 1-(2,5-dihydroxyl-4-aminomethyl phenyl) ethyl ketone, Tert. Butyl Hydroquinone, 2, the 5-methyl dihydroxy benzoate, (2, the 5-dihydroxy phenyl) acetate, 2,4, the 5-trihydroxybenzoic acid, 4,7-dihydroxyl-3-methyl isophthalic acid-indone, 2,5-two chlorohydroquinones, tetrafluoro-Resorcinol, 2, the 5-dihydric ethyl benzoate, 2-(2,5-dihydroxy-benzene methylene radical) propane dinitrile, 2-bromo-1, the 4-Benzenediol, (2, the 5-dihydroxy phenyl) ethyl acetate, 1-(2,4,5-trihydroxy-phenyl)-the 1-butanone, 2,5-dihydroxyl-4-methoxyl methyl benzoate, 2,6-dinitrobenzene-1, the 4-Benzenediol, 2,4,5-trihydroxy-phenyl L-Ala, (2, the 5-dihydroxy phenyl)-(phenyl) ketone, 2,5-di-t-butyl-1, the 4-Benzenediol, 2-(6-methylheptyl)-1, the 4-Benzenediol, 2-(1,1,3, the 3-tetramethyl butyl)-1, the 4-Benzenediol, 2,5-dihydroxyl terephthalic acid dimethyl ester, 2,4,5-three chloro-3,6-dihydroxy phenyl cyanogen, 2,5-two tert-pentyls-1,4-Benzenediol, 2,5-two bromo-1, the 4-Benzenediol, 2,4-diethyl-3,6-dihydroxyl-phosphenylic acid dimethyl ester, pyrocatechol, 2,3-naphthalene glycol, the 5-methyl isophthalic acid, 2,3-benzene triol, the 4-methyl pyrocatechol, the 3-methyl pyrocatechol, the 3-fluoro pyrocatechol, 3-methoxyl group pyrocatechol, 4-chlorine pyrocatechol, 4,5-dichloro pyrocatechol, the 4-tert-butyl catechol, 3,4,5,6-tetrachloro-1,2-Benzenediol, 3-sec.-propyl-6-methyl pyrocatechol, the 3-tertiary butyl-6-methyl pyrocatechol, 3,4-dihydroxy phenyl cyanogen, 3,5-di-t-butyl pyrocatechol, 3,5-di-isopropyl pyrocatechol, 3, the 4-Dihydroxy benzaldehyde, 4-(1,1,3, the 3-tetramethyl butyl)-1, the 2-Benzenediol, 4-(1, the 2-dihydroxy ethyl)-1, the 2-Benzenediol, 1-(3, the 4-dihydroxy phenyl) ethyl ketone, 3, the 4-resorcylic acid, 3,4,5-trihydroxybenzene methane amide, 4-nitro-1, the 2-Benzenediol, 4-(2-amino-1-hydroxyethyl)-1, the 2-Benzenediol, 5-methyl-3-(1,1,3, the 3-tetramethyl butyl)-1, the 2-Benzenediol, (3, the 4-dihydroxy phenyl) acetate, 2-(3,4-dihydroxy-benzene methylene radical) propane dinitrile, 3,5-dinitrobenzene-1,2-Benzenediol, 3, the 4-methyl dihydroxy benzoate, 2-chloro-1-(3, the 4-dihydroxy phenyl) ethyl ketone, phenyl (2,3,4-trihydroxy-phenyl) ketone, 3,4,5-trihydroxybenzoic acid isopropyl ester, 3,4-dihydroxyl-2-aminomethyl phenyl L-Ala, 3-bromo-4, the 5-resorcylic acid, 2-(3,4-dihydroxyl-5-anisole methylene radical) propane dinitrile, 3-(3, the 4-dihydroxy phenyl) ethyl propionate, 2-phenyl-1-(2,3,4-trihydroxy--phenyl) ethyl ketone and 3,4,5-trihydroxy--N-(2-hydroxyethyl) benzamide.
3. curable antiseepage composition according to claim 1, wherein, there are one or more fillers, and it is selected from: silica powder, fused silica, amorphous silica, talcum, granulated glass sphere, graphite, carbon black, aluminum oxide, clay and nanoclay, mica, vermiculite, aluminium nitride, boron nitride, metal-powder, tinsel, poly-(zellon), poly-(chlorotrifluoroethylene), poly-(vinylidene chloride), CaO, BaO, Na
2SO
4, CaSO
4, MgSO
4, zeolite, silica gel, P
2O
5, CaCl
2And Al
2O
3
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201310096501 CN103224608A (en) | 2006-03-30 | 2006-03-30 | Heat-curable epoxy-amine anti-seepage sealant |
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| CN 201310096501 CN103224608A (en) | 2006-03-30 | 2006-03-30 | Heat-curable epoxy-amine anti-seepage sealant |
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| CNA2006800540253A Division CN101405321A (en) | 2006-03-30 | 2006-03-30 | Hot curable epoxy-amine anti-seepage fluid sealant |
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Application publication date: 20130731 |