CN116622315A - Dual-system cured epoxy adhesive and preparation method thereof - Google Patents

Dual-system cured epoxy adhesive and preparation method thereof Download PDF

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Publication number
CN116622315A
CN116622315A CN202210134937.2A CN202210134937A CN116622315A CN 116622315 A CN116622315 A CN 116622315A CN 202210134937 A CN202210134937 A CN 202210134937A CN 116622315 A CN116622315 A CN 116622315A
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China
Prior art keywords
epoxy
adhesive
epoxy resin
parts
dual
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CN202210134937.2A
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Chinese (zh)
Inventor
任华
占重光
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NANJING ZHANYI TECHNOLOGY CO LTD
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NANJING ZHANYI TECHNOLOGY CO LTD
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Priority to CN202210134937.2A priority Critical patent/CN116622315A/en
Publication of CN116622315A publication Critical patent/CN116622315A/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
    • C08G59/20—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 epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/226—Mixtures of di-epoxy compounds
    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
    • 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
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • 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
    • C08G2170/00—Compositions for adhesives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
    • Y02E60/10—Energy storage using batteries

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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)
  • Epoxy Resins (AREA)
  • Adhesives Or Adhesive Processes (AREA)

Abstract

The invention discloses a dual-system cured epoxy adhesive and a preparation method thereof. The double-curing system of the epoxy resin end is introduced into the adhesive, the epoxy resin simultaneously contains double bonds capable of being copolymerized by free radicals and epoxy groups capable of undergoing ring-opening reaction, the crosslinking density of the colloid is greatly improved by the double-curing system formed by crosslinking, the introduction of the third item is reduced, the adhesive is endowed with excellent cohesive strength and heat resistance, meanwhile, the compactness of the product is improved, the ageing and corrosion of water and oxygen to the colloid are further prevented, and the adhesive service life is prolonged. In addition, efficient photo-curing also imparts a higher initial viscosity to the colloid. The adhesive has the advantages of high bonding strength, good temperature resistance, good weather resistance and the like.

Description

Dual-system cured epoxy adhesive and preparation method thereof
Technical Field
The invention relates to the field of adhesives, in particular to an epoxy adhesive with dual-system curing and a preparation method thereof.
Background
The epoxy resin adhesive is an engineering adhesive prepared from an epoxy resin base material, a curing agent, a diluent and an accelerator. The adhesive has the advantages of high adhesive strength, uniform stress distribution, light weight, simple and convenient adhesive process, low cost, high temperature resistance, corrosion resistance and the like, so that the adhesive is widely applied to the fields of household appliances, automobiles, water conservancy traffic, electronic appliances and aerospace industry in recent decades.
It is well known that the adhesive strength of epoxy adhesives is mainly determined by polar groups such as hydroxyl groups, ester bonds, epoxy groups and the like in the molecular chain of the resin and the crosslinking density of the whole cured colloid, so that in order to improve the adhesive strength of a crosslinking agent system, the two are mainly optimized in the industry, such as an epoxy-acrylic hybrid adhesive of China patent CN110352225A, which relates to a two-component adhesive which comprises core/shell rubber and exhibits good T-peel strength and is based on a hybrid urethane-acrylate epoxide, and an acrylate modified polyurethane system is introduced into the epoxy adhesive to improve the adhesiveness, flexibility and T-peel strength of the colloid; the invention discloses a special dual-curing epoxy adhesive for an automobile camera AA process of China patent CN113480958A, a preparation method and application thereof, and discloses an acrylate functional group anhydride monomer with two active groups, wherein the monomer can be crosslinked with epoxy groups, and can be subjected to photo/thermal copolymerization with additionally added (methyl) acrylate monomers to form a dual-network crosslinking structure. In order to improve the adhesive force and the crosslinking density of the epoxy adhesive, a large amount of acrylic resin is added in the patent, and the compatibility of the resin and the epoxy resin and the self-generated defect inevitably affect the heat resistance and corrosion resistance of the whole colloid. Therefore, the heat resistance and mechanical strength of the existing double-system cross-linked epoxy resin adhesive still have a large optimization space.
Disclosure of Invention
In order to further improve the performances of heat resistance, mechanical strength and the like of the epoxy resin adhesive and solve the problem of influence of compatibility, heat resistance and corrosion resistance caused by introducing second-system acrylic resin, the invention provides a novel epoxy adhesive with a double-system curing structure. .
The technical scheme adopted by the invention is as follows:
the double-system cured epoxy adhesive is prepared from the following raw materials in parts by weight:
the double-system cured epoxy resin is a resin containing carbon-carbon double bonds and epoxy groups in the molecular structure; the monomer-based cured epoxy resin is a resin containing only epoxy groups in a molecular structure.
Preferably, the dual system cured epoxy resin is at least one of diallyl bisphenol a epoxy resin, 1, 2-epoxy-4-vinylcyclohexane or 1, 2-epoxy-8-nonene.
Preferably, the monomer-based cured epoxy resin is at least one of bis ((3, 4-epoxycyclohexyl) methyl) adipate, triglycidyl para-aminophenol or a novolac epoxy resin.
Preferably, the phenolic epoxy resin is at least one of o-cresol formaldehyde epoxy resin, phenol type phenolic epoxy resin or bisphenol A type phenolic epoxy resin.
Preferably, the toughening agent is polyvinyl butyral.
Preferably, the reactive diluent is at least one of n-butyl glycidyl ether, propenyl glycidyl ether, phenyl glycidyl ether and the like.
Preferably, the photoinitiator is at least one of 2-hydroxy-methylphenyl propane-1-one (1173), 2- (3' -acryloyloxy) -propoxy-thioxanthone, 1-hydroxycyclohexylphenyl ketone (184), or 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide (TPO).
Preferably, the epoxy curing agent is at least one of polyetheramine D-230, polyetheramine D-400, polyetheramine D-2000, triethyltetramine or triethanolamine.
The preparation method of the dual-system cured epoxy adhesive comprises the following steps:
s1: sequentially adding 5-10 parts of reactive diluent, 30-50 parts of double-system cured epoxy resin, 20-40 parts of monomer cured epoxy resin and 1-5 parts of toughening agent into a 250ml three-neck flask, heating to 60-80 ℃ and uniformly stirring;
s2: and adding 0.5-5 parts of photoinitiator and 1-15 parts of epoxy curing agent into the system, continuously stirring uniformly, and carrying out vacuum defoaming to obtain the dual-system cured epoxy adhesive.
The beneficial effects are that:
the dual-system cured epoxy resin adhesive adopts a dual-system curing and monomer curing epoxy resin compounding process, and solves the problems of reduced compatibility, heat resistance, corrosion resistance and the like caused by the traditional introduction of a second acrylic resin crosslinking system by introducing a dual-curing system at the end of epoxy resin; the crosslinking density of the curing system is further improved by introducing triglycidyl para-aminophenol, phenolic epoxy resin and other multifunctional groups, the compactness of the product is improved, and finally, the product is endowed with excellent heat resistance and shearing strength.
Meanwhile, the mode that the high-efficiency photoinitiation and the thermal polymerization are combined is adopted, the high-efficiency photocuring is utilized to endow the adhesive with high initial viscosity, so that the workpiece can be well fixed before entering the oven, hidden troubles such as dislocation and looseness of the bonding part of the workpiece in the carrying process are prevented, the bonding precision of the workpiece is further improved, and the purpose of bonding performance is achieved through the later-stage thermal polymerization. Meanwhile, the higher crosslinking density further prevents the aging and corrosion of water and oxygen on colloid, and prolongs the bonding life of the colloid.
The specific embodiment is as follows:
the present invention will be described in detail by way of examples, which are not intended to limit the scope of the invention.
In the examples below, the materials used are all commercially available and the methods used are all conventional in the art.
E-51 epoxy resin and diallyl bisphenol A epoxy resin purchased from Anhui Maofu New Material technology Co., ltd
1, 2-epoxy-4-vinylcyclohexane and 1, 2-epoxy-8-nonene purchased from Hubei ferry chemical Co., ltd
Bis ((3, 4-epoxycyclohexyl) methyl) adipate purchased from Hubei Jusheng technology Co., ltd
Triglycidyl para-aminophenol purchased from Asparagus chemical Co., ltd
O-cresol formaldehyde epoxy resin purchased from Baling petrochemical industry
Phenol type phenolic epoxy resin purchased from Jiangyin Wan Qian chemical Co., ltd
Polyvinyl butyral is purchased from Hubei Guang Australia biotechnology Co., ltd
N-butyl glycidyl ether and propenyl glycidyl ether were purchased from Hubei Wande chemical Co., ltd
2-hydroxy-methyl-phenyl-propan-1-one (1173), 1-hydroxy-cyclohexyl-phenyl-methanone (184) were purchased from Hubei Jiachu biological medicine Co., ltd
2,4, 6-Trimethylbenzoyl-diphenylphosphine oxide (TPO) was purchased from Hubei Xinrun De chemical Co., ltd
Polyetheramine D-400, polyetheramine D-2000 was purchased from Aite (Shandong) New Material Co., ltd
Triethyltetramine purchasing from atanan Ming Wei chemical Co., ltd
Embodiment one:
the adhesive comprises the following specific formula (parts by weight):
the manufacturing method comprises the following steps:
into a 250ml three-neck flask, 7 parts of n-butyl glycidyl ether, 30 parts of diallyl bisphenol A epoxy resin, 10 parts of 1, 2-epoxy-8-nonene, 28 parts of bis ((3, 4-epoxycyclohexyl) methyl) adipate, 10 parts of o-cresol formaldehyde epoxy resin and 5 parts of polyvinyl butyral are sequentially added, and the mixture is heated to 75 ℃ and stirred uniformly.
1.2 parts of photoinitiator 2-hydroxy-methyl phenyl propane-1-ketone (1173), 0.8 part of 2,4, 6-trimethyl benzoyl-diphenyl phosphine oxide (TPO) and 5 parts of epoxy curing agent polyether amine D-400 and 3 parts of triethyltetramine are added into the system, and the mixture is continuously and uniformly stirred and defoamed under reduced pressure, so that the dual-system cured epoxy adhesive A is obtained.
Embodiment two:
the adhesive comprises the following specific formula (parts by weight):
the manufacturing method comprises the following steps:
10 parts of propenyl glycidyl ether, 35 parts of 1, 2-epoxy-4-vinylcyclohexane, 30 parts of triglycidyl para-aminophenol, 7 parts of phenol type phenolic epoxy resin and 3 parts of polyvinyl butyral are sequentially added into a 250ml three-neck flask, heated to 75 ℃ and stirred uniformly.
1.2 parts of photoinitiator 1-hydroxycyclohexyl phenyl ketone (184) and 0.8 part of 2,4, 6-trimethyl benzoyl-diphenyl phosphine oxide (TPO) and 12 parts of epoxy curing agent polyetheramine D-2000 are added into the system, and the mixture is continuously stirred uniformly and subjected to vacuum defoaming, so that the dual-system curing epoxy adhesive B is obtained.
Embodiment III:
the adhesive comprises the following specific formula (parts by weight):
the manufacturing method comprises the following steps:
10 parts of n-butyl glycidyl ether, 25 parts of diallyl bisphenol A epoxy resin, 20 parts of 1, 2-epoxy-4-vinylcyclohexane, 10 parts of triglycidyl para-aminophenol, 13 parts of bis ((3, 4-epoxycyclohexyl) methyl) adipate, 8 parts of o-cresol formaldehyde epoxy resin and 2 parts of polyvinyl butyral are sequentially added into a 250ml three-neck flask, and the mixture is heated to 80 ℃ and stirred uniformly.
1.2 parts of photoinitiator 2-hydroxy-methyl phenyl propane-1-ketone (1173), 1.8 parts of 2,4, 6-trimethyl benzoyl-diphenyl phosphine oxide (TPO) and 5 parts of epoxy curing agent polyether amine D-400,4 parts of triethyltetramine are added into the system, and the mixture is continuously stirred uniformly and subjected to vacuum deaeration, so that the double-system cured epoxy adhesive C is obtained.
Comparative example
The common E-51 bisphenol A epoxy resin is adopted to replace double-system cured epoxy resin and monomer cured epoxy resin to participate in the preparation of the adhesive, and the specific formula is as follows:
the manufacturing method comprises the following steps:
10 parts of n-butyl glycidyl ether, 76 parts of E-51 epoxy resin and 5 parts of polyvinyl butyral are sequentially added into a 250ml three-neck flask, heated to 80 ℃ and stirred uniformly.
5 parts of triethyltetramine serving as an epoxy curing agent polyether amine D-400,4 parts is added into the system, and the mixture is continuously stirred uniformly and defoamed under reduced pressure to obtain the common epoxy adhesive.
Examples comparative examples
The dual-system cured epoxy adhesive A, B, C prepared in the examples 1-3 and the common epoxy adhesive prepared in the comparative example are respectively adhered to the surface of transparent glass, and are cured for 1min by UV-LED light with the wavelength of 365nm and the light power of 50W, and are baked for 30min at 100 ℃, and then the tensile shear strength and the glass transition temperature Tg are respectively tested as shown in the table 1.
Test method of tensile shear Strength reference GB/T7124 adhesive tensile shear Strength determination (rigid Material vs rigid Material)
Test methods for glass transition temperature Tg reference is made to GB/T11998 method for determining the glass transition temperature of plastics (thermomechanical analysis)
TABLE 1
As can be seen from Table 1, the shear strength and heat resistance of the dual-system cured epoxy adhesive of the invention are significantly higher than those of the epoxy resin adhesive of the common single-curing system.

Claims (9)

1. The double-system cured epoxy adhesive is characterized by being prepared from the following raw materials in parts by weight:
the double-system cured epoxy resin is a resin containing carbon-carbon double bonds and epoxy groups in the molecular structure; the monomer-based cured epoxy resin is a resin containing only epoxy groups in a molecular structure.
2. The dual system cure epoxy adhesive of claim 1, wherein the dual system cure epoxy resin is at least one of diallyl bisphenol a epoxy resin, 1, 2-epoxy-4-vinyl cyclohexane, or 1, 2-epoxy-8-nonene.
3. The dual system cure epoxy adhesive of claim 1, wherein the monomeric curing epoxy resin is at least one of bis ((3, 4-epoxycyclohexyl) methyl) adipate, triglycidyl para-aminophenol, or phenolic epoxy resin.
4. A dual system cure epoxy adhesive according to claim 3 wherein the phenolic epoxy resin is at least one of an ortho-cresol novolac epoxy resin, a phenol novolac epoxy resin or a bisphenol a novolac epoxy resin.
5. The dual system cure epoxy adhesive of claim 1, wherein the toughening agent is polyvinyl butyral.
6. The dual system cure epoxy adhesive of claim 1, wherein the reactive diluent is at least one of n-butyl glycidyl ether, propenyl glycidyl ether, phenyl glycidyl ether, and the like.
7. The dual system cure epoxy adhesive of claim 1, wherein the photoinitiator is at least one of 2-hydroxy-methylphenyl propane-1-one (1173), 2- (3' -acryloyloxy) -propoxy-thioxanthone, 1-hydroxycyclohexylphenyl ketone (184), or 2,4, 6-trimethylbenzoyl-diphenyl phosphine oxide (TPO).
8. The dual system cure epoxy adhesive of claim 1, wherein the epoxy curing agent is at least one of polyetheramine D-230, polyetheramine D-400, polyetheramine D-2000, triethyltetramine or triethanolamine.
9. A method for preparing a dual-system cured epoxy adhesive as claimed in any one of claims 1 to 8, comprising the steps of:
s1: sequentially adding 5-10 parts of reactive diluent, 30-50 parts of double-system cured epoxy resin, 20-40 parts of monomer cured epoxy resin and 1-5 parts of toughening agent into a 250ml three-neck flask, heating to 60-80 ℃ and uniformly stirring;
s2: and adding 0.5-5 parts of photoinitiator and 1-15 parts of epoxy curing agent into the system, continuously stirring uniformly, and carrying out vacuum defoaming to obtain the dual-system cured epoxy adhesive.
CN202210134937.2A 2022-02-14 2022-02-14 Dual-system cured epoxy adhesive and preparation method thereof Pending CN116622315A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202210134937.2A CN116622315A (en) 2022-02-14 2022-02-14 Dual-system cured epoxy adhesive and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202210134937.2A CN116622315A (en) 2022-02-14 2022-02-14 Dual-system cured epoxy adhesive and preparation method thereof

Publications (1)

Publication Number Publication Date
CN116622315A true CN116622315A (en) 2023-08-22

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Application Number Title Priority Date Filing Date
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Country Status (1)

Country Link
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