CN112126404B - Bismaleimide/epoxy resin/cyanate ester ternary polymerization high-temperature adhesive and preparation method thereof - Google Patents
Bismaleimide/epoxy resin/cyanate ester ternary polymerization high-temperature adhesive and preparation method thereof Download PDFInfo
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- CN112126404B CN112126404B CN202011008081.1A CN202011008081A CN112126404B CN 112126404 B CN112126404 B CN 112126404B CN 202011008081 A CN202011008081 A CN 202011008081A CN 112126404 B CN112126404 B CN 112126404B
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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
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/04—Non-macromolecular additives inorganic
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
- C08L2205/035—Polymer mixtures characterised by other features containing three or more polymers in a blend containing four or more polymers in a blend
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a bismaleimide/epoxy resin/cyanate ester ternary polymerization high-temperature adhesive and a preparation method thereof. The raw materials comprise cyanate ester resin, epoxy resin, bismaleimide resin, a toughening agent, a catalyst, an antioxidant, an ultraviolet light absorber, a thixotropic agent, a coupling agent and a solvent. The adhesive of the invention has bimaleic/epoxy resin/cyanate ester ternary polymerization, greatly improves various performances of single cyanate ester resin; the preparation reaction time is short, the temperature range is large, and the control is easy; all resins in the system react fully and completely, so that the overall performance of the adhesive is improved while the conversion rate of raw materials is improved; the curing process is simple and convenient, the temperature requirement is low, and the time is saved; improve the light aging resistance and toughness of the synthetic resin.
Description
Technical Field
The invention relates to the field of polymer synthetic resin, in particular to a preparation method of a bismaleimide, epoxy resin and cyanate ester resin ternary polymerization high-temperature adhesive.
Background
Cyanate ester resin CE, generally referred to as a dihydric phenol derivative containing two or more-OCN functional groups, can undergo a cyclotrimerization reaction under heating or at a catalyst temperature to form a high-crosslinking-degree network structure macromolecule containing a triazine ring.
The BMI is prepared by crosslinking maleic anhydride and aromatic diamine at high temperature by using a bifunctional compound with maleimide as an active end group.
The epoxy resin EP generally refers to a high molecular epoxy oligomer containing two or more epoxy groups, which reacts with the epoxy groups to form a thermosetting product using aliphatic, alicyclic, aromatic or the like as a skeleton.
The reactions occurring in the ternary resin copolymerization system are complex and mainly may exist: BCE auto-polymerization, BMI auto-polymerization, BCE and BMI copolymerization, and BCE and EP copolymerization.
Cyanate ester has excellent heat resistance, radiation resistance, dielectric property and the like, but the defects are obvious: high brittleness, high curing temperature, high toxicity and the like; the bismaleimide is various in types, is easy to cure and add, has a compact structure after curing, has excellent strength and electrical insulation, but has poor impact resistance, high brittleness and poor solubility; various groups such as epoxy group and ether bond in the epoxy resin structure provide excellent mechanical property, bonding property, electrical property, stability and the like for the epoxy resin.
Disclosure of Invention
The invention aims to provide a bismaleimide/epoxy resin/cyanate ester ternary polymerization high-temperature adhesive and a preparation method thereof. The high-temperature adhesive prepared by the bismaleimide/epoxy resin/cyanate ester ternary polymerization has the advantages of the bismaleimide/epoxy resin/cyanate ester ternary polymerization, and various performances of a single cyanate ester resin are greatly improved, so that the high-temperature adhesive has a wider application direction; the addition of various auxiliaries also endows the adhesive with more additional functions, and the overall efficiency of the adhesive is improved.
The invention provides a bismaleimide/epoxy resin/cyanate ester ternary polymerization high-temperature adhesive, which consists of the following components in percentage by weight:
30 to 50 parts of cyanate ester resin, 0.003 to 0.005 part of catalyst, 10 to 20 parts of epoxy resin, 15 to 30 parts of bismaleimide resin, 0.1 to 5 parts of toughening agent, 0.1 to 5 parts of antioxidant, 0.1 to 10 parts of ultraviolet absorber, 0.1 to 5 parts of thixotropic agent, 0.1 to 5 parts of coupling agent and 5 to 40 parts of solvent.
The cyanate resin comprises bisphenol A cyanate, bisphenol L cyanate, bisphenol M cyanate, or the like, or a mixture of any one or more of phenolic cyanate and dicyclopentadiene cyanate.
The bismaleimide resin comprises any one or a mixture of 4, 4-diphenylmethane bismaleimide, N-m-phenylene bismaleimide, 4-diphenyl ether bismaleimide and the like.
The epoxy resin comprises one or more of F51 epoxy resin, E51 epoxy resin, AG80 epoxy resin, TDE85 epoxy resin and the like.
The solvent comprises one or more of N, N-dimethylformamide, absolute ethyl alcohol, xylene or cyclohexanone and the like.
The catalyst comprises one or more of dibutyltin dilaurate, cobalt oxalate, ferric triacetylacetonate and other organic metal salts and a mixture of monophenol.
The toughening agent comprises one or more of polysulfone, polyethersulfone, polyphenylene oxide or polyetherimide and the like.
The antioxidant comprises one of antioxidant 1010, antioxidant 1017 or a compound of antioxidant 168.
The ultraviolet light absorber comprises any one or a mixture of more of UV-O, UV-9, UV-P or UV-328 and the like.
The thixotropic agent comprises a mixture of any one or more of organobentonite, hydrogenated castor oil, polyamide wax or fumed silica.
The coupling agent comprises any one or a mixture of KH550, KH560, KH570 and the like.
The invention also provides a preparation method of the bismaleimide/epoxy resin/cyanate ester ternary polymerization high-temperature adhesive, which comprises the following steps: according to the weight, 30 to 50 parts of cyanate ester resin is completely melted at the temperature of below 100 ℃, and 0.0003 to 0.0005 part of catalyst is immediately dropped into the cyanate ester resin and polymerized for 30 to 60 minutes; melting and self-polymerizing 15-30 parts of bismaleimide resin at 200 ℃ for 30-60 min; then mixing the cyanate ester and the bismaleimide resin while the cyanate ester and the bismaleimide resin are hot, adding 0.1 to 5 parts of flexibilizer, and copolymerizing for 40 to 90min at the temperature of between 150 and 200 ℃; then cooling to 100-150 ℃, and adding 0.1-5 parts of antioxidant and 0.1-10 parts of ultraviolet absorber; after being dispersed evenly, 10 to 20 portions of epoxy resin, 0.1 to 5 portions of thixotropic agent and 0.1 to 5 portions of coupling agent are added, and the mixture is continuously copolymerized for 30 to 60 minutes under heat preservation; and cooling to below 30 ℃, adding 5-40 parts of solvent and 0.0027-0.0045 parts of catalyst, and uniformly dispersing to obtain the cyanate/bismaleimide/epoxy copolymer high-temperature adhesive. Stirring is required throughout the preparation.
The adhesive curing process comprises the following steps: 150 ℃/3h +180 ℃/3h +220 ℃/4 h.
The invention has the beneficial effects that: the preparation reaction time is short, the temperature range is large, and the control is easy; all resins in the system react fully and completely, so that the overall performance of the adhesive is improved while the conversion rate of raw materials is improved; the curing process is simple and convenient, the temperature requirement is low, and the time is saved; improve the light aging resistance and toughness of the synthetic resin.
Detailed Description
The invention will now be further described with reference to the following examples:
example 1
Weighing 100g of bisphenol A type cyanate ester resin in a three-neck flask, stirring and heating to 80 ℃ until the bisphenol A type cyanate ester resin is melted; after the materials are completely melted, 0.001g of dibutyltin dilaurate is immediately dropped in, and the mixture is stirred for 30min under heat preservation; weighing 60g of 4, 4-diphenylmethane bismaleimide resin, melting at 170 ℃, keeping the temperature and stirring for 30min, pouring bisphenol A cyanate into the 4, 4-diphenylmethane bismaleimide, adding 10g of polysulfone, keeping the temperature and stirring at 170 ℃, and copolymerizing for 40 min; then cooling to 120 ℃, and adding 10g of antioxidant 1010 and 10 gUV-O; after the mixture is uniformly dispersed, adding 40g of F51 epoxy resin, 10g of polyamide wax and 10g of KH550, and continuing to perform heat preservation copolymerization; after 30min, the temperature was reduced to below 30 ℃, and 80g of a xylene/N, N-dimethylformamide mixed solution and 0.009g of dibutyltin dilaurate were added to obtain an uncured resin.
After curing at 150 ℃/3h +180 ℃/3h +220 ℃/4h, testing according to the national standard, and obtaining the following results: the tensile shear strength at room temperature is 20.8MPa, the tensile shear strength at 220 ℃ is 18.7MPa, and the shear impact strength at room temperature is 6.5kJ/m 2 220 ℃ shear impact strength of 5.7kJ/m 2 Dielectric constant 3.11, light resistance grade four.
Example 2
Weighing 200g of bisphenol M type cyanate ester resin in a three-neck flask, stirring and heating to melt the bisphenol M type cyanate ester resin; after the mixture is completely melted, slowly dripping a mixture of 0.002g of ferric triacetylacetonate and nonylphenol with the purity of 5 percent, and stirring for 30min at the temperature of 80 ℃; weighing 120g of 4, 4-diphenyl ether bismaleimide resin, melting at 170 ℃, and stirring for 30min under heat preservation; pouring bisphenol M cyanate into 4, 4-diphenyl ether bismaleimide after enough time, adding 20g of polyether sulfone, keeping the temperature at 170 ℃, stirring and copolymerizing for 40 min; then cooling to 120 ℃, and adding 20g of antioxidant 1017 and 8 gUV-P; after the mixture is uniformly dispersed, 80g of AG80 epoxy resin, 20g of organic bentonite and 20g of KH570 are added, and the heat preservation and copolymerization are continuously carried out; after 30min, the temperature is reduced to below 30 ℃, and 160g of cyclohexanone/N, N-dimethylformamide mixed solution and 0.018g of ferric triacetylacetonate and nonylphenol mixture with the purity of 5 percent are added to obtain the uncured resin.
After curing at 150 ℃/3h +180 ℃/3h +220 ℃/4h, testing according to the national standard, and obtaining the following results: room temperature tensile shear strength of 19.6MPa, 220 ℃ tensile shear strength of 17.3MPa, and room temperature shear impact strength of 6.7kJ/m 2 Shear impact strength at 220 ℃ of 5.9kJ/m 2 Dielectric constant 3.04, light resistance grade four.
Example 3
Weighing 45g of dicyclopentadiene cyanate ester resin into a three-neck flask, and stirring and heating the flask until the dicyclopentadiene cyanate ester resin is melted; after the materials are completely melted, 0.0005g of dibutyltin dilaurate is immediately and slowly dropped in, and the mixture is stirred for 30min under the condition of heat preservation at 80 ℃; weighing 24g of N, N-m-phenylene bismaleimide resin, melting at 170 ℃, preserving heat and stirring for 30 min; pouring dicyclopentadiene cyanate into N, N-m-phenylene bismaleimide after enough time, adding 4g of polyphenyl ether, keeping the temperature at 170 ℃, stirring and copolymerizing for 40 min; then cooling to 120 ℃, and adding 4g of antioxidant 168 and 8 gUV-328; after the mixture is uniformly dispersed, 16g of TDE85 epoxy resin, 4g of hydrogenated castor oil and 4g of KH560 are added, and the heat preservation and copolymerization are continuously carried out; after 30min, the temperature is reduced to below 30 ℃, and 32g of ethanol/N, N-dimethylformamide mixed solution and 0.004g of dibutyltin dilaurate are added to obtain the uncured resin.
After curing at 150 ℃/3h +180 ℃/3h +220 ℃/4h, testing according to the national standard, and obtaining the following results: tensile shear strength at room temperature of 20.1MPa and tensile shear strength at 220 DEG C19.2MPa, and the room-temperature shear impact strength is 6.6kJ/m 2 Shear impact strength at 220 ℃ of 5.9kJ/m 2 Dielectric constant 2.97, light fastness level four.
Comparative example:
weighing 100g of bisphenol A type cyanate ester resin in a three-neck flask, and stirring and heating; weighing 60g of 4, 4-diphenylmethane bismaleimide resin at 170 ℃, pouring the 4, 4-diphenylmethane bismaleimide resin into bisphenol A cyanate ester, preserving heat, stirring and copolymerizing for 60 min; then cooling to 120 ℃, adding 40g of F51 epoxy resin, and continuing heat preservation and copolymerization; after 30min, the temperature is reduced and 80g N, N-dimethylformamide is added to obtain the uncured resin.
After curing at 120 ℃/3h +150 ℃/3h +180 ℃/3h +200 ℃/3h and post-processing at 220 ℃/4h, testing according to the national standard, and the result is as follows: 17.9MPa of room-temperature tensile shear strength, 14.1MPa of 220 ℃ tensile shear strength and 5.1kJ/m of room-temperature shear impact strength 2 Shear impact strength at 220 ℃ of 3.8kJ/m 2 Dielectric constant 4.35, light resistance grade two.
From the comparison of the examples with the comparative examples it can be concluded that: compared with the traditional preparation process of the cyanate ester high-temperature adhesive, the preparation process of the bismaleimide, the epoxy resin and the cyanate ester resin ternary copolymer resin has the advantages that the reaction time is greatly shortened, the reaction temperature range is wider, and the control is easy; the curing process is simpler, more convenient and faster, thereby saving a large amount of time and cost; compared with the product obtained by the traditional preparation method, the mechanical property, the electrical property and the light aging resistance of the cured resin are greatly improved; the whole preparation process has no obvious by-product, and the health of workers is ensured; all resins in the system react fully and completely, so that the overall performance of the adhesive is improved while the conversion rate of raw materials is improved; the various auxiliary agents also enable the adhesive to have more additional properties, thereby having wider application.
The present disclosure has been described in terms of the above-described embodiments, which are merely exemplary of the implementations of the present disclosure. It must be noted that the disclosed embodiments do not limit the scope of the disclosure. Rather, variations and modifications are possible within the spirit and scope of the disclosure, and these are all within the scope of the disclosure.
Claims (8)
1. The bismaleimide/epoxy resin/cyanate ester ternary polymerization high-temperature adhesive is characterized by comprising the following components in parts by weight:
the preparation method of the bismaleimide/epoxy resin/cyanate ester ternary polymerization high-temperature adhesive comprises the following steps: according to weight, 30 to 50 parts of cyanate ester resin is melted at the temperature of below 100 ℃, 0.0003 to 0.0005 part of catalyst is immediately dropped into the melted cyanate ester resin and polymerized for 30 to 60 minutes, 15 to 30 parts of bismaleimide resin is melted at the temperature of 200 ℃ and polymerized for 30 to 60 minutes, then the cyanate ester and the bismaleimide resin are mixed while hot, 0.1 to 5 parts of flexibilizer is added and copolymerized for 40 to 90 minutes at the temperature of 150 to 200 ℃, then the temperature is reduced to 100 to 150 ℃, 0.1 to 5 parts of antioxidant and 0.1 to 10 parts of ultraviolet absorber are added, 10 to 20 parts of epoxy resin is added after the uniform dispersion, 0.1-5 parts of thixotropic agent and 0.1-5 parts of coupling agent, continuously preserving heat and copolymerizing for 30-60 min, finally cooling to below 30 ℃, adding 5-40 parts of solvent and 0.0027-0.0045 parts of catalyst to obtain the cyanate/bismaleimide/epoxy copolymerization high-temperature adhesive, and continuously stirring in the whole process; the adhesive curing process comprises the following steps: 150 ℃/3h +180 ℃/3h +220 ℃/4 h.
2. The bismaleimide/epoxy/cyanate ester terpolymer high temperature adhesive of claim 1, wherein the cyanate ester resin comprises any one or more of bisphenol a cyanate ester, bisphenol L cyanate ester, bisphenol M cyanate ester, or phenol-formaldehyde cyanate ester, and dicyclopentadiene cyanate ester.
3. The bismaleimide/epoxy/cyanate ester terpolymer high temperature adhesive of claim 1, wherein the bismaleimide resin comprises any one or a mixture of 4, 4-diphenylmethane bismaleimide, N-m-phenylene bismaleimide, 4-diphenyl ether bismaleimide.
4. The bismaleimide/epoxy/cyanate ester terpolymer high temperature adhesive of claim 1, wherein the epoxy resin comprises any one or more of F51 epoxy, E51 epoxy, AG80 epoxy or TDE85 epoxy.
5. The bismale/epoxy/cyanate ester terpolymer high temperature adhesive of claim 1, wherein the catalyst comprises any one or more of dibutyl tin dilaurate, cobalt oxalate, ferric triacetylacetonate organometallic salts in combination with monophenols.
6. The bismaleimide/epoxy/cyanate ester terpolymer high temperature adhesive according to claim 1, wherein the solvent comprises one or more of N, N-dimethylformamide, absolute ethanol, xylene or cyclohexanone; the toughening agent comprises one or more of polysulfone, polyethersulfone, polyphenylene oxide or polyetherimide; the antioxidant comprises one of antioxidant 1010, antioxidant 1017 or a compound with antioxidant 168; the ultraviolet light absorber comprises any one or mixture of UV-O, UV-9, UV-P or UV-328.
7. The bismaleimide/epoxy/cyanate ester terpolymer high temperature adhesive of claim 1, wherein: the thixotropic agent comprises a mixture of any one or more of organobentonite, hydrogenated castor oil, polyamide wax or fumed silica.
8. The bismaleimide/epoxy/cyanate ester terpolymer high temperature adhesive of claim 1, wherein the coupling agent comprises a mixture of any one or more of KH550, KH560 or KH 570.
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| CN114149764A (en) * | 2021-12-14 | 2022-03-08 | 长春长光宇航复合材料有限公司 | Ultrathin high-toughness cyanate ester adhesive film and preparation method thereof |
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| US4110364A (en) * | 1974-03-19 | 1978-08-29 | Mitsubishi Gas Chemical Company, Inc. | Curable resin compositions of cyanate esters |
| US5350635A (en) * | 1992-12-22 | 1994-09-27 | Minnesota Mining And Manufacturing Company | Cyanate resin adhesive for polyimide film |
| CN101531880B (en) * | 2009-04-28 | 2012-01-11 | 黑龙江省科学院石油化学研究院 | Canate-bimaleimide resin adhesive and preparation method |
| CN101885900A (en) * | 2010-07-02 | 2010-11-17 | 广东生益科技股份有限公司 | Resin composition, bonding sheet and copper-clad plate made using same, manufacturing method thereof |
| CN103074026A (en) * | 2013-01-11 | 2013-05-01 | 西北工业大学 | Bismaleimide/cyanate ester resin adhesive resisting to temperature as high as 220 DEG C and preparation method |
| CN106753218B (en) * | 2016-12-12 | 2019-12-03 | 西南科技大学 | A kind of low dielectric high tenacity cyanate ester adhesive and preparation method thereof |
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