CN117363293A - Flexible epoxy adhesive composition - Google Patents

Flexible epoxy adhesive composition Download PDF

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Publication number
CN117363293A
CN117363293A CN202311480301.4A CN202311480301A CN117363293A CN 117363293 A CN117363293 A CN 117363293A CN 202311480301 A CN202311480301 A CN 202311480301A CN 117363293 A CN117363293 A CN 117363293A
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parts
adhesive composition
epoxy adhesive
amine
flexible epoxy
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CN202311480301.4A
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Inventor
江其郑
张鸿赐
张全全
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Xiamen Youbai Electronic Materials Co ltd
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Xiamen Youbai Electronic Materials Co ltd
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Priority to CN202311480301.4A priority Critical patent/CN117363293A/en
Publication of CN117363293A publication Critical patent/CN117363293A/en
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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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/62—Alcohols or phenols
    • C08G59/621—Phenols
    • C08G59/623—Aminophenols

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The application relates to the technical field of epoxy adhesives, and particularly provides a flexible epoxy adhesive composition. The flexible epoxy adhesive composition comprises the following raw materials in parts by weight: 100 parts of epoxy resin, 0-25 parts of diluent, 0-50 parts of curing agent and 5-50 parts of modified phenolic amine; the modified phenolic amine is obtained by reacting phenolic amine with polyurethane prepolymer and/or polyurea prepolymer. The epoxy adhesive composition of the present application can maintain a higher tensile strength even at a higher shear strength after curing.

Description

Flexible epoxy adhesive composition
Technical Field
The application relates to the technical field of epoxy adhesives, in particular to a flexible epoxy adhesive composition.
Background
Epoxy adhesives require high flexibility to function as adhesives, typically by incorporating a number of flexible additives into the adhesive formulation. One type of flexibilizer commonly used is a long chain alkyl phenol such as dodecylphenol, cardanol, and the like. The long-chain alkyl phenol can improve the flexibility of the epoxy adhesive and can accelerate the curing rate of the epoxy resin due to the existence of phenolic hydroxyl. But the independent long-chain alkyl phenol is used as a flexible auxiliary agent, so that the mechanical strength of the epoxy adhesive is greatly influenced. One modification method is to graft long chain hydrocarbyl phenol onto the structure of epoxy resin, for example, chinese patent No. 113512390a discloses that the reaction of basic epoxy resin and phenolic hydroxyl material produces a highly flexible epoxy resin. Another modification method is modification of long chain alkylphenols by subjecting long chain alkylphenols, long chain alkylamines and formaldehyde (such as paraformaldehyde) to a mannich reaction together using a phenolic amine condensation reaction, as exemplified below,
the polyamine structure is introduced on the benzene ring of the long-chain alkylphenol, and the polyamine structure can be used as a toughening agent and a curing agent of an epoxy adhesive, such as a D.E.H.85 curing agent of DOW chemistry in America.
Disclosure of Invention
The introduction of the phenolic amine can endow the epoxy resin with lower curing temperature (which can be close to 0 ℃), flexibility, water resistance and the like, but simultaneously the mechanical strength of the epoxy resin is obviously reduced. For this reason, the inventors have further modified the structure of the phenolic amine. Based thereon, the present application provides a flexible epoxy adhesive composition.
The application adopts the following technical scheme:
a flexible epoxy adhesive composition comprises the following raw materials in parts by weight: 100 parts of epoxy resin, 0-25 parts of diluent, 0-50 parts of curing agent and 5-50 parts of modified phenolic amine;
the modified phenolic amine is obtained by reacting phenolic amine with polyurethane prepolymer and/or polyurea prepolymer.
Preferably, the phenolic amine is prepared by reacting long-chain alkyl phenol, polyamine and paraformaldehyde according to a molar ratio of 1:1-2:1-2.
More preferably, the long-chain alkylphenol is selected from one or a combination of several of cardanol, dodecylphenol and nonylphenol.
More preferably, the polyamine has the formula NH 2 R 1 NHR 2 Wherein R is 1 Selected from C2-C10 alkylene, C4-C10 substituted alkylene or C8-C12 arylene, R 2 Selected from H or OH.
Preferably, the isocyanate content of the polyurethane prepolymer and the polyurea prepolymer is not less than 3wt%, respectively.
Preferably, the molar sum of primary amino groups and hydroxyl groups in the phenolic amine and the molar sum of isocyanate groups in the polyurethane prepolymer and/or polyurea prepolymer are in a ratio of 1-1.1:1.
Preferably, the epoxy resin is selected from one or a combination of a plurality of basic epoxy resins and modified epoxy resins.
Preferably, the diluent is selected from one or a combination of more of inert diluent and reactive diluent.
Preferably, the curing agent is one or a combination of more than one of fatty amine and derivative curing agent thereof, polyamide and derivative curing agent thereof, aromatic amine and derivative thereof, alicyclic amine and derivative curing agent thereof and polyether amine and derivative curing agent thereof.
Preferably, the raw material component further comprises: 0.3-1 part of flatting agent, 0.3-0.8 part of wetting agent, 0.4-1 part of defoamer, 0.5-2 parts of thixotropic agent, 10-50 parts of filler, 1-2 parts of coupling agent and 0.1-2 parts of pigment.
In summary, the present application has the following beneficial effects:
1. according to the epoxy adhesive, on the basis of a phenolic amine structure, polyurethane prepolymer and/or polyurea prepolymer are utilized, the phenolic amine structure is grafted to two ends of polyurethane and/or polyurea to form an ABA-like block copolymer, wherein A is the phenolic amine structure, B is the polyurethane and/or polyurea structure, and on the basis of retaining the performances of high reactivity, high flexibility and the like of the phenolic amine, the toughness and the strength of the polyurethane and/or polyurea are combined, so that the epoxy adhesive still has high mechanical strength on the basis of high flexibility.
2. The modified phenolic amine combines the characteristics of phenolic amine and polyurethane/polyurea, has the flexibility effect of the phenolic amine and polyurethane/polyurea on the epoxy resin, and solves the problem that the mechanical strength of the epoxy resin is obviously reduced due to the larger structure of the modified phenolic amine.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below.
Throughout the specification, unless specifically indicated otherwise, the terms used herein should be understood as meaning as commonly used in the art. Accordingly, unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In case of conflict, the present specification will control.
The application provides a flexible epoxy adhesive composition, which comprises the following raw materials in parts by weight: 100 parts of epoxy resin, 0-25 parts of diluent, 0-50 parts of curing agent and 5-50 parts of modified phenolic amine;
the modified phenolic amine is obtained by reacting phenolic amine with polyurethane prepolymer and/or polyurea prepolymer.
The modified phenolic amine disclosed by the application is characterized in that amino or hydroxyl on the phenolic amine is reacted with terminal isocyanate groups of polyurethane prepolymer and/or polyurea prepolymer to form a block copolymer structure similar to ABA, wherein A is a phenolic amine structure, and B is a polyurethane or polyurea structure. The modified phenolic amine combines the flexibility, low-temperature reaction and other characteristics of the phenolic amine, the toughness and high strength characteristics of the polyurethane/polyurea prepolymer, and has a larger molecular structure, so that the flexibility of the epoxy resin is improved, and the influence on the mechanical strength is low.
In a preferred embodiment of the present application, the phenolic amine is prepared by reacting a long chain hydrocarbyl phenol, a polyamine, and paraformaldehyde in a molar ratio of 1:1 to 2:1 to 2. Specifically, the long-chain alkylphenol can be selected from one or a combination of several of cardanol, dodecylphenol and nonylphenol. Specifically, the general formula of the polyamine is NH 2 R 1 NHR 2 Wherein R is 1 Selected from C2-C10 alkylene, C4-C10 substituted alkylene or C8-C12 arylene, R 2 Selected from H or OH. Further, the polyamine may be represented as H (NH (CH) 2 ) m ) n NHR 2 Wherein m can be 2-5, n can be 1-5, R 2 The meaning is as above. As examples, the polyamine may be hexamethylenediamine, 1, 4-butanediamine, 1, 6-hexamethylenediamine, divinyl triamine, tetraethylenepentamine, N-hydroxyethyl ethylenediamine, N-hydroxyethyl diethylenetriamine, N-hydroxyethyl triethylenetetramine, N-hydroxyethyl tetraethylenepentamine, N-hydroxypropyl ethylenediamineEthylenediamine, N-hydroxypropyl diethylenetriamine, N-hydroxypropyl triethylenetetramine, and the like. One terminal primary amino group in the polyamine participates in the mannich reaction, and the other terminal, primary amino group or hydroxyl group may continue to react with the polyurethane prepolymer and/or polyurea prepolymer.
In a preferred embodiment of the present application, the isocyanate content of the polyurethane prepolymer and the polyurea prepolymer, respectively, is not less than 3% by weight. Further, the isocyanate content of the polyurethane prepolymer and the polyurea prepolymer is not less than 5wt%, respectively. Polyurethane prepolymers may be obtained by reacting polyisocyanates with polyols, as is well known in the art. Polyurea prepolymers may be obtained by reacting a polyisocyanate with a secondary amino compound such as an aspartate, as is well known in the art.
In a preferred embodiment of the present application, the molar sum of primary amino groups and hydroxyl groups in the phenolic amine and the molar sum of isocyanate groups in the polyurethane prepolymer and/or polyurea prepolymer are in a ratio of 1 to 1.1:1. Within the above molar ratio range, the ABA block copolymer as described above can be formed more favorably. For example, the molar sum of primary amino groups and hydroxyl groups in the phenolic amine and the molar sum of isocyanate groups in the polyurethane prepolymer and/or polyurea prepolymer can be 1:1, 1.01:1, 1.02:1, 1.04:1, 1.03:1, 1.05:1, 1.06:1, 1.07:1, 1.08:1, 1.09:1, 1.1:1, etc.
In a preferred embodiment of the present application, the epoxy resin is selected from one or a combination of several of a base epoxy resin and a modified epoxy resin. In the present application, the base epoxy resin refers to an unmodified epoxy resin such as bisphenol a type epoxy resin, bisphenol F epoxy resin, bisphenol S epoxy resin, alicyclic epoxy resin, or the like. The modified epoxy resin refers to the modification of the basic epoxy resin by adopting other structures, such as polyurethane modified epoxy resin, organosilicon modified epoxy resin, organic fluorine modified epoxy resin, acrylic modified epoxy resin and the like.
In a preferred embodiment of the present application, the diluent is selected from one or a combination of inert diluents and reactive diluents. Inert diluents refer to diluents that need to be removed during or after curing, such as ethylene glycol methyl ether acetate, diethylene glycol monomethyl ether, and the like, without participating in the curing reaction of the epoxy resin. Reactive diluents are small organic compounds which can participate in the curing reaction of epoxy resins, typically containing epoxide groups, and examples thereof include toluene glycidyl ether, trimethylolpropane triglycidyl ether, neodecanoic acid glycidyl ester, castor oil polyglycidyl ether, butyl glycidyl ether, glycerol epoxy resin, resorcinol diglycidyl ether, benzyl glycidyl ether, hexyl glycidyl ether, C12-14 alkyl glycidyl ether and the like.
In a preferred embodiment of the present application, the curing agent is selected from one or a combination of several of aliphatic amine and its derivative curing agent, polyamide and its derivative curing agent, alicyclic amine and its derivative curing agent, and polyether amine and its derivative curing agent. The curing agent of fatty amine and its derivative may be ethylenediamine, propylenediamine, diethylenetriamine, triethylenetetramine, amine adducts thereof, etc.; the aromatic amine and its derivative may be m-phenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, etc.; the alicyclic amine and its derivative curing agent may be methylcyclohexyldiamine, 4 '-diaminodicyclohexylmethane, 3' -dimethyl-4, 4-diaminodicyclohexylmethane, etc.; the curing agent of the polyetheramine and the derivative thereof can be polyetheramine D230, polyetheramine D400, polyetheramine D-2000, etc.
In a preferred embodiment of the present application, the feed composition further comprises: 0.3-1 part of flatting agent, 0.3-0.8 part of wetting agent, 0.4-1 part of defoamer, 0.5-2 parts of thixotropic agent, 10-50 parts of filler, 1-2 parts of coupling agent and 0.1-2 parts of pigment. The thixotropic agent can be fumed silica, attapulgite, organic bentonite and the like. The filler may be calcium carbonate (such as light calcium carbonate, heavy calcium carbonate, nano calcium carbonate, etc.), talc, mica powder, clay, wollastonite, alumina powder, aluminum hydroxide powder, aluminum silicate, titanium dioxide, carbon black, glass powder, glass spheres, etc.
The raw material components of the flexible epoxy adhesive composition of the present application may further contain 0.01 to 0.2 parts of a curing accelerator such as an imidazole compound, a tertiary amine compound, an imidazoline compound, and the like.
The preparation method of the flexible epoxy adhesive composition can be as follows: mixing the other raw materials except the curing agent and the modified phenolic amine uniformly, adding the curing agent and the modified phenolic amine, and mixing uniformly to obtain the modified phenolic amine.
The following describes the technical scheme of the present application in detail with reference to preparation examples, examples and comparative examples. Unless otherwise indicated, the parts in the examples and comparative examples below are parts by weight.
Preparation examples 1-3 preparation of modified phenolic amine
Preparation example 1
Adding 1 mole part of cardanol and 1 mole part of ethylenediamine into a reaction bottle, introducing nitrogen for protection, heating to 65 ℃, stirring until the solution is uniform, adding 1.2 mole parts of paraformaldehyde for four times within 1 hour, continuously stirring, continuously heating to 80 ℃ after the addition is finished, reacting for 0.5 hour, reducing the pressure to-0.07 to-0.08 MPa, and removing low-boiling substances to obtain the phenolic amine.
The reaction vessel was purged with nitrogen, isophorone diisocyanate and polyether diol (average molecular weight 400) were added to the reaction vessel at a molar ratio of 1:0.7, stirred at room temperature for 1 hour, and heated to 70 ℃ and stirred for 1 hour continuously to obtain a polyurethane prepolymer, and the NCO content was measured to be 5.1wt%.
And (3) introducing nitrogen into a reaction vessel for protection, adding the phenolic amine and the polyurethane prepolymer into the reaction vessel according to the molar ratio of the primary amino groups to the isocyanate groups of 1:1, adding the weight of the phenolic amine and the polyurethane prepolymer and 0.1% of dibutyltin dilaurate, and heating to 80 ℃ for reaction for 2 hours to obtain the modified phenolic amine.
Preparation example 2
Adding 1 mole part of dodecylphenol and 1.5 mole parts of divinylbenzene into a reaction bottle, introducing nitrogen for protection, heating to 65 ℃, stirring until the solution is uniform, adding 1.4 mole parts of paraformaldehyde for four times within 1 hour, continuously stirring, continuously heating to 80 ℃ for reacting for 1 hour, reducing the pressure to-0.099 MPa, and removing low-boiling substances to obtain the phenolic amine.
The reaction vessel was purged with nitrogen, hexamethylene diisocyanate and aspartic acid ester (obtained by reacting diethyl fumarate and 1, 6-hexamethylenediamine in a molar ratio of 2:1) were added to the reaction vessel in a molar ratio of 1:0.7, stirred at room temperature for 6 hours, warmed to 50℃and stirred for 2 hours, and a polyurea prepolymer was obtained, which was found to have an NCO content of 5.2% by weight.
And (3) introducing nitrogen into a reaction vessel for protection, adding the phenolic amine and polyurea prepolymer into the reaction vessel according to the molar ratio of primary amino groups to isocyanate groups of 1.02:1, adding 0.12% of dibutyltin dilaurate by weight of the phenolic amine and polyurea prepolymer, and heating to 80 ℃ for reaction for 2 hours to obtain the modified phenolic amine.
Preparation example 3
In preparation 2, the molar ratio of hexamethylene diisocyanate to aspartic acid ester was adjusted from 1:0.7 to 1:0.65. The remaining steps remain unchanged.
Example 1
The epoxy adhesive composition comprises 100 parts of epoxy resin E-44, 10 parts of butyl glycidyl ether, 11 parts of 1, 6-hexamethylenediamine and 5 parts of modified phenolic amine of preparation example 1.
Uniformly mixing the epoxy resin E-44 and butyl glycidyl ether, adding modified phenolic amine, uniformly mixing, adding 1, 6-hexamethylenediamine, and continuously uniformly mixing to obtain the epoxy adhesive composition.
Example 2
The differences between example 2 and example 1 are: the modified phenolic amine in example 1 was adjusted from 5 parts to 20 parts. The remaining steps remain unchanged.
Example 3
Example 3 differs from example 1 in that: the modified phenolic amine in example 1 was adjusted from 5 parts to 35 parts. The remaining steps remain unchanged.
Example 4
Example 4 differs from example 1 in that: the modified phenolic amine in example 1 was adjusted from 5 parts to 50 parts. The remaining steps remain unchanged.
Example 5
The epoxy adhesive composition comprises 100 parts of epoxy resin E-51, 10 parts of butyl glycidyl ether, 2 parts of white carbon black, 20 parts of hollow glass beads with average particle size of 2 mu m, 0.6 part of dimethyl silicone oil defoamer, 1.5 parts of methyltrimethoxysilane coupling agent, 0.7 part of polyether modified silicone oil wetting agent, 30 parts of polyether amine D230 and 15 parts of modified phenolic amine of preparation example 1.
Uniformly mixing epoxy resin E-51 and butyl glycidyl ether, sequentially adding hollow glass beads, a dimethyl silicone oil defoamer, a polyether modified silicone oil wetting agent, a silane coupling agent and white carbon black, uniformly dispersing, adding modified phenolic amine, uniformly mixing, adding polyether amine D230, and continuously uniformly mixing to obtain the epoxy adhesive composition.
Example 6
The differences between example 6 and example 5 are: the modified phenolic amine of preparation example 1 was prepared in example 5 by adjusting the same parts by weight of the modified phenolic amine of preparation example 2. The remaining steps remain unchanged.
Example 7
The differences between example 7 and example 5 are: the modified phenolic amine of preparation example 1 was prepared in example 5 by adjusting the same parts by weight of the modified phenolic amine of preparation example 3. The remaining steps remain unchanged.
Comparative example 1
The difference between comparative example 1 and example 1 is: no modified phenolic amine was added in example 1. The remaining steps remain unchanged.
Comparative example 2
The difference between comparative example 2 and example 5 is: the modified phenolic amine in example 5 was adjusted to an equivalent weight of the phenolic amine of preparation 1. The remaining steps remain unchanged.
Comparative example 3
The difference between comparative example 2 and example 5 is: the modified phenolic amine in example 5 was adjusted to an equal weight combination of phenolic amine of preparation 1 and polyurethane prepolymer of preparation 1 in a molar ratio of 1:1. The remaining steps remain unchanged.
Comparative example 4
The difference between comparative example 2 and example 5 is: the modified phenolic amine in example 5 was adjusted to an equal weight of cardanol. The remaining steps remain unchanged.
The epoxy adhesive compositions of examples 1-7 and comparative examples 1-4 were uniformly coated on aluminum sheet-aluminum sheet test pieces and cured at room temperature for 48 hours. The aluminum sheet-aluminum sheet test pieces were bonded to each other in dimensions of 25mm×25mm×10mm and 45mm×25mm×20 mm. Tensile shear strength was measured according to GB/T7124-2008.
The epoxy adhesive compositions of examples 1-7 and comparative examples 1-4 were uniformly coated on a polytetrafluoroethylene substrate and cured at room temperature for 48 hours to form a film. The tensile strength of the membrane is tested by adopting an electronic tensile machine.
The results are shown in Table 1 below.
TABLE 1 Performance test results
As can be seen from the data in table 1, the addition of modified phenolic amine to the epoxy adhesive significantly improved the tensile shear strength of the epoxy adhesive. Comparative example 5 and comparative example 4, the modified phenolic amine had similar shear strength as compared to cardanol, but the tensile strength was significantly higher. In comparative examples 5 and 2, the modified phenolic amine had higher tensile and shear strengths than the phenolic amine.
The present embodiment is merely illustrative of the present application and is not intended to be limiting, and those skilled in the art, after having read the present specification, may make modifications to the present embodiment without creative contribution as required, but is protected by patent laws within the scope of the claims of the present application.

Claims (10)

1. A flexible epoxy adhesive composition is characterized by comprising the following raw material components in parts by weight: 100 parts of epoxy resin, 0-25 parts of diluent, 0-50 parts of curing agent and 5-50 parts of modified phenolic amine;
the modified phenolic amine is obtained by reacting phenolic amine with polyurethane prepolymer and/or polyurea prepolymer.
2. The flexible epoxy adhesive composition of claim 1 wherein the phenolic amine is prepared by reacting a long chain hydrocarbyl phenol, a polyamine and paraformaldehyde in a molar ratio of 1:1 to 2:1 to 2.
3. The flexible epoxy adhesive composition of claim 2 wherein the long chain alkyl phenol is selected from one or a combination of several of cardanol, dodecylphenol and nonylphenol.
4. The flexible epoxy adhesive composition of claim 2 wherein the polyamine has the formula NH 2 R 1 NHR 2 Wherein R is 1 Selected from C2-C10 alkyl, C4-C10 substituted alkyl or C8-C12 aryl, R 2 Selected from H or OH.
5. The flexible epoxy adhesive composition of claim 1 wherein the isocyanate content of the polyurethane prepolymer and the polyurea prepolymer are each no less than 3wt%.
6. The flexible epoxy adhesive composition of claim 1 wherein the molar sum of primary amino groups and hydroxyl groups in the phenolic amine to the molar sum of isocyanate groups in the polyurethane and/or polyurea prepolymer is in a ratio of 1 to 1.1:1.
7. The flexible epoxy adhesive composition of claim 1 wherein the epoxy resin is selected from one or a combination of base epoxy resin and modified epoxy resin.
8. The flexible epoxy adhesive composition of claim 1 wherein the diluent is selected from one or a combination of inert diluents and reactive diluents.
9. The flexible epoxy adhesive composition of claim 1 wherein the curing agent is selected from one or a combination of fatty amine and its derivative curing agents, polyamide and its derivative curing agents, aromatic amine and its derivative, alicyclic amine and its derivative curing agents, and polyether amine and its derivative curing agents.
10. The flexible epoxy adhesive composition of claim 1 wherein the raw material components further comprise: 0.3-1 part of flatting agent, 0.3-0.8 part of wetting agent, 0.4-1 part of defoamer, 0.5-2 parts of thixotropic agent, 10-50 parts of filler, 1-2 parts of coupling agent and 0.1-2 parts of pigment.
CN202311480301.4A 2023-11-08 2023-11-08 Flexible epoxy adhesive composition Pending CN117363293A (en)

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Application Number Priority Date Filing Date Title
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Application Number Priority Date Filing Date Title
CN202311480301.4A CN117363293A (en) 2023-11-08 2023-11-08 Flexible epoxy adhesive composition

Publications (1)

Publication Number Publication Date
CN117363293A true CN117363293A (en) 2024-01-09

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