CN103074027A - Phenolphthalein cyanate/benzoxazine resin adhesive resistant to 250 DEG C and preparation method - Google Patents
Phenolphthalein cyanate/benzoxazine resin adhesive resistant to 250 DEG C and preparation method Download PDFInfo
- Publication number
- CN103074027A CN103074027A CN2013100111955A CN201310011195A CN103074027A CN 103074027 A CN103074027 A CN 103074027A CN 2013100111955 A CN2013100111955 A CN 2013100111955A CN 201310011195 A CN201310011195 A CN 201310011195A CN 103074027 A CN103074027 A CN 103074027A
- Authority
- CN
- China
- Prior art keywords
- parts
- cyanate
- phenolphthalein
- resin
- benzoxazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Abstract
The invention relates to a phenolphthalein cyanate/benzoxazine resin adhesive resistant to 250 DEG C and a preparation method. The adhesive is characterized by comprising the components in parts by weight as follows: 10-60 parts of cyanate ester resin 10-40 parts of bismaleimide resin, 5-30 parts of benzoxazine resin and 10-60 parts of solvents. The preparation method adopts the bismaleimide-modified cyanate ester resin as the matrix, takes diluted benzoxazine resin as the modified filler, utilizes a traditional thermocuring method to prepare the high-temperature-resistant adhesive, and can be widely applied to the high-tech fields such as aerospace, electric power, electronics and the like. The adhesive and the preparation method have the advantages that the bismaleimide resin and the benzoxazine resin are added into the phenolphthalein cyanate ester resin, so that reinforcing and toughening functions are performed; and simultaneously, the heat resistance of various added substances is excellent, therefore, formed groups are provided with good heat resistance, and various performances of the adhesive are improved.
Description
Technical field
The invention belongs to resistant to elevated temperatures tackiness agent, be specifically related to the anti-250 ℃ of high temperature adhesives of a kind of phenolphthalein cyanate/benzoxazine resin and preparation method, can be widely used in the high-tech areas such as aerospace, electric power, electronics.
Background technology
In recent years, along with the progress of science and technology, the performance of high-temperature resistance adhesive improves constantly, and is widely used in various high-tech sectors, is particularly bringing into play irreplaceable vital role at field high-temperature resistance adhesives such as Aeronautics and Astronautics, electronics.Simultaneously, these fields are also more and more high to the requirement of the high thermal resistance of tackiness agent.For example: guided missile or spaceship will stand high temperature gas flow and wash away when reentrying, and surface temperature can reach 2300-2600 ℃, need high-temperature resistance adhesive to be used for the bonding of ceramic insulation watt; Modern supersonic aircraft (Mach number M=3.0-3.5) is in high-speed flight, the outside surface local temperature of honeycomb cellular structure member is up to 260-316 ℃, and the internal temperature of honeycomb structure is also up to 200-260 ℃, this just needs tackiness agent except the material to honeycomb structure has good adhesiveproperties, also must have excellent resistance to elevated temperatures.High temperature resistance organic adhesives not only will keep good physical condition under working temperature, and must keep the stable of chemical structure in time limit of service, can not degrade.At present research is more, the wider high temperature resistance organic adhesives of application mainly contains epoxy resin, polyimide, resol class and polyurethanes etc.
Summary of the invention
The technical problem that solves
For fear of the deficiencies in the prior art part, the present invention proposes the anti-250 ℃ of high temperature adhesives of a kind of phenolphthalein cyanate/benzoxazine resin and preparation method, the tackiness agent of preparation excellent heat resistance.This tackiness agent aspect the high-temperature insulation of space flight, boats and ships, weapons, nuclear industry and electric express locomotive and the manufacturing of matrix material and copper-clad plate have great importance.
Technical scheme
The anti-250 ℃ of high temperature adhesives of a kind of phenolphthalein cyanate/benzoxazine resin is characterized in that component comprises: 10～60 parts of cyanate ester resins, 10～40 parts of bimaleimide resins, 5～30 parts of benzoxazine colophonies, 10～60 parts of solvents; Described part is weight part.
Described cyanate ester resin is bisphenol A cyanate ester resin or phenolphthalein type cyanate ester resin, or its both mixture.
Described bimaleimide resin is ditane type bismaleimides or diallyl type bismaleimides, or its both mixture.
Described benzoxazine colophony compound is any in bisphenol A-type benzoxazine colophony, the bis-phenol M type benzoxazine colophony, or its both mixture.
Described solvent is the mixture of any or its many persons in dehydrated alcohol, dimethyl formamide, dimethylbenzene, pimelinketone, N,N-DIMETHYLACETAMIDE, toluene or the trieline.
The preparation process of described phenolphthalein type cyanate ester resin is as follows:
Step 1: with the tetrahydrofuran (THF) of 90 parts of dryings, BrCN and 18 parts of phenolphthalein of 13 parts, at-20 ℃ of low-temp reactions;
Step 2: at N
2Under the atmosphere, 11.5 parts of triethylamines are dropwised with 2h;
Step 3: system temperature is risen to 8 ℃, react 3h under this temperature, reaction mixture is filtered, filtrate is through the Rotary Evaporators decompression and solvent recovery, and room temperature leaves standstill the adularescent material to be separated out;
Step 4:, wash with the NaOH solution gradation of 1mol/L this substance dissolves with methylene dichloride, until methylene dichloride no longer reddens mutually.Again with the distillation washing, until neutral;
Step 5: through Rotary Evaporators reclaim under reduced pressure methylene dichloride, the residual solution room temperature leaves standstill, and has solids to separate out.With acetone solid matter is migrated out Rotary Evaporators, then pour in the frozen water, obtain the phenolphthalein cyanate ester monomer;
Step 6: then dry, purification obtains phenolphthalein cyanate resin alicyclic monomer;
Described part is mass parts.
A kind of method for preparing described phenolphthalein cyanate/anti-250 ℃ of high temperature adhesives of benzoxazine resin is characterized in that step is as follows:
Step 1: after 10～60 parts of cyanate ester resins and 10～40 parts of bimaleimide resins were mixed, melting and copolymerization 20min～100min obtained cyanate/bimaleimide resin under 120～200 ℃ temperature;
Step 2: to 80～130 ℃ temperature, the solvent of 5～30 parts of benzoxazine colophonies and 10～60 parts is poured in the cyanate/bimaleimide resin of pre-polymerization, and melting copolymerization 20min～60min, obtain the anti-250 ℃ of high temperature adhesives of phenolphthalein cyanate/benzoxazine colophony.
The curing of a kind of phenolphthalein cyanate/anti-250 ℃ of high temperature adhesives of benzoxazine resin is characterized in that: curing process is 150 ℃/1h+200 ℃/2h+220 ℃/4h, last 250 ℃/4h of aftertreatment.
Beneficial effect
A kind of phenolphthalein cyanate that the present invention proposes/anti-250 ℃ of high temperature adhesives of benzoxazine resin and preparation method, employing contains Cyanate Resin Modified by Prepolymer of Bismaleimide as matrix, to dilute benzoxazine colophony as modified filler, utilize the resistant to elevated temperatures tackiness agent of traditional thermal curing methods preparation, can be widely used in the high-tech areas such as aerospace, electric power, electronics.
The advantage of the anti-250 ℃ of high temperature adhesives of phenolphthalein cyanate/benzoxazine colophony of the present invention is: the thermotolerance of synthetic phenolphthalein cyanate ester resin is good than bisphenol A cyanate ester resin.Bimaleimide resin and benzoxazine colophony are joined in the phenolphthalein cyanate ester resin, play the toughness reinforcing effect of enhancing.Owing to the excellent heat resistance of each material that adds, the group of formation has good thermotolerance simultaneously, thereby improves the properties of tackiness agent.
Embodiment
Now the invention will be further described in conjunction with the embodiments:
Embodiment 1
Take by weighing 40 parts of synthetic phenolphthalein cyanate ester resins in there-necked flask, be heated to melting, then add 30 part 4,4 '-ditane type bismaleimides heated and stirred gets the A component, at 120～200 ℃ of reaction 20min～100min; Then adjust the temperature to 80～130 ℃, under this temperature with 40 parts of N, N '-dimethyl formamide and 5 parts of benzoxazine colophonies are poured into condensing reflux in the A component of there-necked flask, and melting copolymerization 20min～60min, namely obtain the anti-250 ℃ of high temperature adhesives of phenolphthalein cyanate/benzoxazine colophony.Its curing process is: 150 ℃/1h+200 ℃/2h+220 ℃/4h, and last 250 ℃/4h of aftertreatment.
By national standard test shearing resistance, test-results is: room temperature tensile shearing resistance 21.2MPa, 250 ℃ of tensile shear strength 13.4MPa.
After processing 200h under 250 ℃ of hot conditionss, experimental result is: room temperature tensile shearing resistance 20.7MPa, 250 ℃ of tensile shear strength 12.6MPa.
Embodiment 2
Take by weighing 40 parts of synthetic phenolphthalein cyanate ester resins in there-necked flask, be heated to melting, then add 20 part 4,4 '-ditane type bismaleimides heated and stirred gets the A component, at 120～200 ℃ of reaction 20min～100min; Then adjust the temperature to 80～130 ℃, under this temperature with 20 parts of N, N '-dimethyl formamide, 10 parts of dimethylbenzene, 10 parts of pimelinketone and 10 parts of benzoxazine colophonies are poured into condensing reflux in the A component of there-necked flask, and melting copolymerization 20min～60min, namely obtain the anti-250 ℃ of high temperature adhesives of phenolphthalein cyanate/benzoxazine colophony.Its curing process is: 150 ℃/1h+200 ℃/2h+220 ℃/4h, and last 250 ℃/4h of aftertreatment.
By national standard test shearing resistance, test-results is: room temperature tensile shearing resistance 23.5MPa, 250 ℃ of tensile shear strength 14.2MPa.
After processing 200h under 250 ℃ of hot conditionss, experimental result is: room temperature tensile shearing resistance 21.9MPa, 250 ℃ of tensile shear strength 13.3MPa.
Embodiment 3
Take by weighing 40 parts of synthetic phenolphthalein cyanate ester resins in there-necked flask, be heated to melting, then add 10 part 4,4 '-ditane type bismaleimides heated and stirred gets the A component, at 120～200 ℃ of reaction 20min～100min; Then adjust the temperature to 80～130 ℃, under this temperature with 20 parts of N, N '-dimethyl formamide, 20 parts of dimethylbenzene, 10 parts of pimelinketone and 20 parts of benzoxazine colophonies are poured into condensing reflux in the A component of there-necked flask, and melting copolymerization 20min～60min, namely obtain the anti-250 ℃ of high temperature adhesives of phenolphthalein cyanate/benzoxazine colophony.Its curing process is: 150 ℃/1h+200 ℃/2h+220 ℃/4h, and last 250 ℃/4h of aftertreatment.
By national standard test shearing resistance, test-results is: room temperature tensile shearing resistance 20.9MPa, 250 ℃ of tensile shear strength 12.6MPa.
After processing 200h under 250 ℃ of hot conditionss, experimental result is: room temperature tensile shearing resistance 19.7MPa, 250 ℃ of tensile shear strength 11.9MPa.
Embodiment 4:
Take by weighing 20 parts of synthetic phenolphthalein cyanate ester resins and 20 parts of bisphenol A cyanate ester resins in there-necked flask, be heated to melting, then add 30 part 4,4 '-ditane type bismaleimides heated and stirred gets the A component, at 120～200 ℃ of reaction 20min～100min; Then adjust the temperature to 80～130 ℃, under this temperature with 40 parts of N, N '-dimethyl formamide and 5 parts of benzoxazine colophonies are poured into condensing reflux in the A component of there-necked flask, and melting copolymerization 20min～60min, namely obtain the anti-250 ℃ of high temperature adhesives of phenolphthalein cyanate/benzoxazine colophony.Its curing process is: 150 ℃/1h+200 ℃/2h+220 ℃/4h, and last 250 ℃/4h of aftertreatment.
By national standard test shearing resistance, test-results is: room temperature tensile shearing resistance 21.3MPa, 250 ℃ of tensile shear strength 12.7MPa.
After processing 200h under 250 ℃ of hot conditionss, experimental result is: room temperature tensile shearing resistance 19.6MPa, 250 ℃ of tensile shear strength 11.3MPa.
Embodiment 5:
Take by weighing 20 parts of synthetic phenolphthalein cyanate ester resins and 20 parts of bisphenol A cyanate ester resins in there-necked flask, be heated to melting, then add 20 part 4,4 '-ditane type bismaleimides heated and stirred gets the A component, at 120～200 ℃ of reaction 20min～100min; Then adjust the temperature to 80～130 ℃, under this temperature with 20 parts of N, N '-dimethyl formamide, 10 parts of dimethylbenzene, 10 parts of pimelinketone and 10 parts of benzoxazine colophonies are poured into condensing reflux in the A component of there-necked flask, and melting copolymerization 20min～60min, namely obtain the anti-250 ℃ of high temperature adhesives of phenolphthalein cyanate/benzoxazine colophony.Its curing process is: 150 ℃/1h+200 ℃/2h+220 ℃/4h, and last 250 ℃/4h of aftertreatment.
By national standard test shearing resistance, test-results is: room temperature tensile shearing resistance 22.9MPa, 250 ℃ of tensile shear strength 13.5MPa.
After processing 200h under 250 ℃ of hot conditionss, experimental result is: room temperature tensile shearing resistance 20.2MPa, 250 ℃ of tensile shear strength 11.9MPa.
Embodiment 6:
Take by weighing 20 parts of synthetic phenolphthalein cyanate ester resins and 20 parts of bisphenol A cyanate ester resins in there-necked flask, be heated to melting, then add 10 part 4,4 '-ditane type bismaleimides heated and stirred gets the A component, at 120～200 ℃ of reaction 20min～100min; Then adjust the temperature to 80～130 ℃, under this temperature with 20 parts of N, N '-dimethyl formamide, 20 parts of dimethylbenzene, 10 parts of pimelinketone and 20 parts of benzoxazine colophonies are poured into condensing reflux in the A component of there-necked flask, and melting copolymerization 20min～60min, namely obtain the anti-250 ℃ of high temperature adhesives of phenolphthalein cyanate/benzoxazine colophony.Its curing process is: 150 ℃/1h+200 ℃/2h+220 ℃/4h, and last 250 ℃/4h of aftertreatment.
By national standard test shearing resistance, test-results is: room temperature tensile shearing resistance 21.1MPa, 250 ℃ of tensile shear strength 11.2MPa.
After processing 200h under 250 ℃ of hot conditionss, experimental result is: room temperature tensile shearing resistance 18.9MPa, 250 ℃ of tensile shear strength 10.3MPa.
Comparative Examples
Take by weighing 40 parts of bisphenol A cyanate ester resins in there-necked flask, be heated to melting, then add 20 part 4,4 '-ditane type bismaleimides heated and stirred gets the A component, at 120～200 ℃ of reaction 20min～100min; Then adjust the temperature to 80～130 ℃, under this temperature with 20 parts of N, N '-dimethyl formamide, 10 parts of dimethylbenzene, 10 parts of pimelinketone and 10 parts of benzoxazine colophonies are poured into condensing reflux in the A component of there-necked flask, and melting copolymerization 20min～60min, namely obtain the anti-250 ℃ of high temperature adhesives of bisphenol A cyanate ester/benzoxazine colophony.Its curing process is: 150 ℃/1h+200 ℃/2h+220 ℃/4h, and last 250 ℃/4h of aftertreatment.
By national standard test shearing resistance, test-results is: room temperature tensile shearing resistance 22.6MPa, 250 ℃ of tensile shear strength 12.3MPa.
After processing 200h under 250 ℃ of hot conditionss, experimental result is: room temperature tensile shearing resistance 20.5MPa, 250 ℃ of tensile shear strength 10.3MPa.
The comparison of embodiment and Comparative Examples, can find out, the phenolphthalein cyanate ester resin more can effectively raise cyanate/benzoxazine colophony high-temperature resistance adhesive tensile shear strength and shearing impact intensity at room temperature than bisphenol A cyanate ester resin, especially the tensile shear strength performance of this tackiness agent is improved under hot conditions, more can satisfy aerospace etc. to the application of high-performance adhesive.
The synthesis step of the used phenolphthalein cyanate ester resin of the present embodiment: add the tetrahydrofuran (THF) of 80ml drying in the there-necked flask of 500ml, system temperature is down to-20 ℃ with the low-temp reaction groove, then add BrCN and the 18g phenolphthalein of 13g.At N
2Under the atmosphere, 11.5g triethylamine (being dissolved to the tetrahydrofuran (THF) of 40ml) is slowly dripped, dropwise through 2h.Then system temperature is risen to 8 ℃, react 3h under this temperature, reaction mixture is filtered, filtrate is through the Rotary Evaporators decompression and solvent recovery, and room temperature leaves standstill the adularescent material to be separated out., wash with the NaOH solution gradation of 1mol/L this substance dissolves with methylene dichloride, until methylene dichloride no longer reddens mutually.With the distillation washing, until neutral (with pH value detection paper), through Rotary Evaporators reclaim under reduced pressure methylene dichloride, the residual solution room temperature leaves standstill, and has solids to separate out again.With acetone solid matter is migrated out Rotary Evaporators, then pour in the preprepared frozen water, utilize the little characteristic of its solubleness in water, obtain the phenolphthalein cyanate ester monomer.Then dry, purification obtains phenolphthalein cyanate resin alicyclic monomer.
Claims (8)
1. the anti-250 ℃ of high temperature adhesives of phenolphthalein cyanate/benzoxazine resin is characterized in that component comprises: 10～60 parts of cyanate ester resins, 10～40 parts of bimaleimide resins, 5～30 parts of benzoxazine colophonies, 10～60 parts of solvents; Described part is weight part.
2. anti-250 ℃ of high temperature adhesives of described phenolphthalein cyanate/benzoxazine resin according to claim 1, it is characterized in that: described cyanate ester resin is bisphenol A cyanate ester resin or phenolphthalein type cyanate ester resin, or its both mixture.
3. anti-250 ℃ of high temperature adhesives of described phenolphthalein cyanate/benzoxazine resin according to claim 1, it is characterized in that: described bimaleimide resin is ditane type bismaleimides or diallyl type bismaleimides, or its both mixture.
4. anti-250 ℃ of high temperature adhesives of described phenolphthalein cyanate/benzoxazine resin according to claim 1, it is characterized in that: described benzoxazine colophony compound is any in bisphenol A-type benzoxazine colophony, the bis-phenol M type benzoxazine colophony, or its both mixture.
5. anti-250 ℃ of high temperature adhesives of described phenolphthalein cyanate/benzoxazine resin according to claim 1 is characterized in that: described solvent is the mixture of any or its many persons in dehydrated alcohol, dimethyl formamide, dimethylbenzene, pimelinketone, N,N-DIMETHYLACETAMIDE, toluene or the trieline.
6. anti-250 ℃ of high temperature adhesives of described phenolphthalein cyanate/benzoxazine resin according to claim 2 is characterized in that:,
It is characterized in that: the preparation process of described phenolphthalein type cyanate ester resin is as follows:
Step 1: with the tetrahydrofuran (THF) of 90 parts of dryings, BrCN and 18 parts of phenolphthalein of 13 parts, at-20 ℃ of low-temp reactions;
Step 2: at N
2Under the atmosphere, 11.5 parts of triethylamines are dropwised with 2h;
Step 3: system temperature is risen to 8 ℃, react 3h under this temperature, reaction mixture is filtered, filtrate is through the Rotary Evaporators decompression and solvent recovery, and room temperature leaves standstill the adularescent material to be separated out;
Step 4:, wash with the NaOH solution gradation of 1mol/L this substance dissolves with methylene dichloride, until methylene dichloride no longer reddens mutually.Again with the distillation washing, until neutral;
Step 5: through Rotary Evaporators reclaim under reduced pressure methylene dichloride, the residual solution room temperature leaves standstill, and has solids to separate out.With acetone solid matter is migrated out Rotary Evaporators, then pour in the frozen water, obtain the phenolphthalein cyanate ester monomer;
Step 6: then dry, purification obtains phenolphthalein cyanate resin alicyclic monomer;
Described part is mass parts.
7. method for preparing any described phenolphthalein cyanate/anti-250 ℃ of high temperature adhesives of benzoxazine resin of claim 1～5 is characterized in that step is as follows:
Step 1: after 10～60 parts of cyanate ester resins and 10～40 parts of bimaleimide resins were mixed, melting and copolymerization 20min～100min obtained cyanate/bimaleimide resin under 120～200 ℃ temperature;
Step 2: to 80～130 ℃ temperature, the solvent of 5～30 parts of benzoxazine colophonies and 10～60 parts is poured in the cyanate/bimaleimide resin of pre-polymerization, and melting copolymerization 20min～60min, obtain the anti-250 ℃ of high temperature adhesives of phenolphthalein cyanate/benzoxazine colophony.
8. the curing of the described phenolphthalein cyanate of claim 1/anti-250 ℃ of high temperature adhesives of benzoxazine resin is characterized in that: curing process is 150 ℃/1h+200 ℃/2h+220 ℃/4h, last 250 ℃/4h of aftertreatment.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013100111955A CN103074027A (en) | 2013-01-11 | 2013-01-11 | Phenolphthalein cyanate/benzoxazine resin adhesive resistant to 250 DEG C and preparation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2013100111955A CN103074027A (en) | 2013-01-11 | 2013-01-11 | Phenolphthalein cyanate/benzoxazine resin adhesive resistant to 250 DEG C and preparation method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103074027A true CN103074027A (en) | 2013-05-01 |
Family
ID=48150730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2013100111955A Pending CN103074027A (en) | 2013-01-11 | 2013-01-11 | Phenolphthalein cyanate/benzoxazine resin adhesive resistant to 250 DEG C and preparation method |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN103074027A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104031385A (en) * | 2014-06-19 | 2014-09-10 | 苏州生益科技有限公司 | High-frequency resin composition, prepreg and laminated board thereof |
| CN104629052A (en) * | 2015-01-16 | 2015-05-20 | 沈阳航空航天大学 | Bismaleimide resin containing cyano group and phthalidyl side group and preparation method thereof |
| CN106221215A (en) * | 2016-08-22 | 2016-12-14 | 威海光威复合材料股份有限公司 | Cyanate ester resin composite material preparation method |
| WO2020068598A1 (en) * | 2018-09-24 | 2020-04-02 | Asml Netherlands B.V. | Target formation apparatus |
| CN115584025A (en) * | 2022-12-07 | 2023-01-10 | 四川泸天化创新研究院有限公司 | Modified BT resin and preparation method thereof |
| RU2797593C1 (en) * | 2022-06-30 | 2023-06-07 | федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский национальный исследовательский технический университет им. А.Н.Туполева-КАИ" | Cyan-benzoxazine composition with low curing temperature and method for its production |
| CN117690902A (en) * | 2024-02-03 | 2024-03-12 | 江门市和美精艺电子有限公司 | Packaging substrate containing modified adhesive film |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0357006A1 (en) * | 1988-08-29 | 1990-03-07 | Cytec Technology Corp. | Structures exhibitting improved transmission of ultrahigh frequency electromagnetic radiation and structural materials which allow their construction |
| CN101531880A (en) * | 2009-04-28 | 2009-09-16 | 黑龙江省科学院石油化学研究院 | Canate-bimaleimide resin adhesive and preparation method |
| CN102732208A (en) * | 2012-07-08 | 2012-10-17 | 西北工业大学 | Modified 250 DEG C high temperature resistant cyanate ester/benzoxazine resin adhesive and preparation method thereof |
-
2013
- 2013-01-11 CN CN2013100111955A patent/CN103074027A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0357006A1 (en) * | 1988-08-29 | 1990-03-07 | Cytec Technology Corp. | Structures exhibitting improved transmission of ultrahigh frequency electromagnetic radiation and structural materials which allow their construction |
| CN101531880A (en) * | 2009-04-28 | 2009-09-16 | 黑龙江省科学院石油化学研究院 | Canate-bimaleimide resin adhesive and preparation method |
| CN102732208A (en) * | 2012-07-08 | 2012-10-17 | 西北工业大学 | Modified 250 DEG C high temperature resistant cyanate ester/benzoxazine resin adhesive and preparation method thereof |
Non-Patent Citations (1)
| Title |
|---|
| 白晓慧等: "酚酞型氰酸酯的合成与表征", 《中国胶粘剂》, vol. 21, no. 8, 31 August 2012 (2012-08-31), pages 4 - 7 * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104031385A (en) * | 2014-06-19 | 2014-09-10 | 苏州生益科技有限公司 | High-frequency resin composition, prepreg and laminated board thereof |
| CN104031385B (en) * | 2014-06-19 | 2016-05-18 | 苏州生益科技有限公司 | A kind of high frequency resin combination and prepreg and laminate |
| CN104629052A (en) * | 2015-01-16 | 2015-05-20 | 沈阳航空航天大学 | Bismaleimide resin containing cyano group and phthalidyl side group and preparation method thereof |
| CN104629052B (en) * | 2015-01-16 | 2017-02-01 | 沈阳航空航天大学 | Bismaleimide resin containing cyano group and phthalidyl side group and preparation method thereof |
| CN106221215A (en) * | 2016-08-22 | 2016-12-14 | 威海光威复合材料股份有限公司 | Cyanate ester resin composite material preparation method |
| CN112753285A (en) * | 2018-09-24 | 2021-05-04 | Asml荷兰有限公司 | Target forming device |
| WO2020068598A1 (en) * | 2018-09-24 | 2020-04-02 | Asml Netherlands B.V. | Target formation apparatus |
| US11448967B2 (en) | 2018-09-24 | 2022-09-20 | Asml Netherlands B.V. | Target formation apparatus |
| RU2797593C1 (en) * | 2022-06-30 | 2023-06-07 | федеральное государственное бюджетное образовательное учреждение высшего образования "Казанский национальный исследовательский технический университет им. А.Н.Туполева-КАИ" | Cyan-benzoxazine composition with low curing temperature and method for its production |
| CN115584025A (en) * | 2022-12-07 | 2023-01-10 | 四川泸天化创新研究院有限公司 | Modified BT resin and preparation method thereof |
| CN115584025B (en) * | 2022-12-07 | 2023-09-26 | 四川泸天化创新研究院有限公司 | Modified BT resin and preparation method thereof |
| CN117690902A (en) * | 2024-02-03 | 2024-03-12 | 江门市和美精艺电子有限公司 | Packaging substrate containing modified adhesive film |
| CN117690902B (en) * | 2024-02-03 | 2024-04-12 | 江门市和美精艺电子有限公司 | Packaging substrate containing modified adhesive film |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN103074027A (en) | Phenolphthalein cyanate/benzoxazine resin adhesive resistant to 250 DEG C and preparation method | |
| CN105802516B (en) | The preparation method of ethanol-soluble type high temperature resistant Phosphate adhesive | |
| CN103805078B (en) | A kind of high tenacity, 250 DEG C of life-time service modified cyanic acid ester structural film adhesives and preparation method thereof | |
| CN103319890B (en) | Polyimide-fiber-fabrpolyimide-resin-basecomposite polyimide-resin-basecomposite composite material and preparation method thereof | |
| CN106977717B (en) | A kind of ester group compound containing alkenyl and preparation method thereof and the bimaleimide resin being modified using it | |
| CN102876247A (en) | Modified cyanate adhesive film and preparation method thereof | |
| CN103131346A (en) | High temperature-resistant carrier adhesive film and preparation method thereof | |
| CN103074026A (en) | Bismaleimide/cyanate ester resin adhesive resisting to temperature as high as 220 DEG C and preparation method | |
| CN108676137B (en) | Aromatic polyimide thermosetting resin and preparation method thereof | |
| CN105367793A (en) | Cyanate ester resin prepolymer with excellent space environment property, and prepreg, preparation method and application thereof | |
| CN101514246B (en) | Modification method of continuous PBO fiber for strengthening interface of bimaleimide resin base composite material | |
| CN104017334A (en) | High-modulus sheet molding compound (SMC) and production method thereof | |
| CN106810863B (en) | A kind of pbo fiber epoxy resin composite material and preparation method thereof | |
| CN103739519A (en) | Low-viscosity nitrile resin monomer, copolymer, cured material and preparation method thereof | |
| CN102732208A (en) | Modified 250 DEG C high temperature resistant cyanate ester/benzoxazine resin adhesive and preparation method thereof | |
| CN111019072A (en) | Phenolic-modified polyether amine type epoxy resin curing agent and preparation method thereof | |
| CN103965824A (en) | Acetenyl polyimide modified cyanate ester adhesive and preparation method thereof | |
| CN1935896A (en) | Epoxy vesin complex and its use | |
| CN112708087A (en) | Nano silicon dioxide modified water-based phenolic resin and preparation method thereof | |
| CN104649702B (en) | A kind of preparation method of high-strength light carbon-fibre composite | |
| CN105238335A (en) | Heat-resistant glue and preparation method thereof | |
| CN104649701A (en) | Preparation method of high-strength light-weight carbon/carbon composite material | |
| CN114249895A (en) | Long-chain hydroxyl-free sulfone ether epoxy resin and preparation method thereof | |
| CN107098795A (en) | A kind of two functions alkenyl phenoxy compounds and preparation method thereof and the dissoluble bismaleimide resin using its modification | |
| CN109207076B (en) | Aluminum silicate ceramic fiber structure adhesive film |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C02 | Deemed withdrawal of patent application after publication (patent law 2001) | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20130501 |