CN102199413A - Modified epoxy resin adhesive used for polyimide flexible copper-clad plate - Google Patents
Modified epoxy resin adhesive used for polyimide flexible copper-clad plate Download PDFInfo
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- CN102199413A CN102199413A CN2011100809120A CN201110080912A CN102199413A CN 102199413 A CN102199413 A CN 102199413A CN 2011100809120 A CN2011100809120 A CN 2011100809120A CN 201110080912 A CN201110080912 A CN 201110080912A CN 102199413 A CN102199413 A CN 102199413A
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Abstract
The invention relates to an epoxy resin adhesive modified by bismaleimide and liquid butadiene nitrile rubber, and a method for manufacturing a polyimide flexible copper-clad plate using the adhesive. The adhesive is composed of a bismaleimide copolymer, liquid rubber-modified epoxy resin, unmodified epoxy resin, filler, a curing agent and an organic solvent. The adhesive can be used for manufacturing a three-layer flexible copper-clad plate composed of a polyimide thin film, the adhesive and a copper foil, and the dip-soldering resisting temperature of the obtained copper-clad plate can reach 365 DEG C.
Description
Technical field
The present invention relates to prepare the adhesive area that the polyimide flexible copper-clad plate is used, the component and the technology of the tackiness agent that particularly resistant to elevated temperatures polyimide flexible copper-clad plate is required.
Background technology
Flexible copper-clad plate (FCCL) is a basic material of producing printed circuit board (PCB), is composited by polyimide (PI) film, tackiness agent and Copper Foil hot pressing usually.FCCL divides two kinds of three ply board and two-plies, and the consumption maximum of three ply board is at present generally made by bonding hot pressing of tackiness agent and after fixing by Kapton or polyester film and Copper Foil.Tackiness agent is one of principal element of decision flexible copper-clad plate performance.The tackiness agent of PI film and Copper Foil of being used to bond generally has acrylic ester and epoxy resin two big classes.In recent years, printed circuit board industry improves constantly the requirement of polyimide copper clad lamination resistance to elevated temperatures, particularly novel process such as pb-free solder needs the FCCL plate can stand higher soldering bath temperature (the anti-weldering temperature of general requirement FCCL plate is more than 260 ℃ when having lead welding to connect), and at high temperature shows enough stability.The raising of this resistance toheat depends on tackiness agent used when preparing copper-clad plate.
Span comes the amide molecule chain rigidity bigger, and higher second-order transition temperature (T is arranged
g), and have excellent heat and a thermo-oxidative stability, the researchist wishes by utilizing span to come acid amides to come modified epoxy to improve its resistance to elevated temperatures (Zhao Limei always, Xia Hua, Gong Rongzhou. the research of bi-maleimide modified phenol aldehyde type epoxy resin. functional materials, 2007,38 (8): 404-407; Li Yuqing, Huang Ying, Yan's pears. bimaleimide resin toughening modifying progress. engineering plastics are used, and 2007,35 (2): 74-76.).But when the practical application of copper-clad plate field, there are several problems: the one, bismaleimides is crisp, and the tackiness agent that directly utilizes its modification to obtain is difficult to be applied to flexible copper-clad plate; The 2nd, the bismaleimides homopolymer is difficult to be dissolved in low boiling point solvents such as acetone, causes the manufacturability behind itself and the epoxy blend relatively poor; The 3rd, the compatibility of itself and epoxy also has problems, and separates out from tackiness agent easily on the macroscopic view.The present invention has prepared a kind of bismaleimides epoxy resin copolymer BDME that dissolves in low boiling point solvent, and the Resins, epoxy EC that adds a kind of liquid acrylonitrile butadiene rubber modification is as toughness reinforcing component, and obtains a kind of polyimide flexible copper-clad plate novel, that have excellent high temperature resistance character after Resins, epoxy and the filler blend and sticks with glue agent.
Summary of the invention
The present invention is directed to the requirement of the better heat-resisting character of flexible copper-clad plate needs, provide span to come the prescription of the combined modified epoxyn of acid amides imines and liquid nbr carboxyl terminal, utilize the method for this formulation tackiness agent, and utilize the tackiness agent of gained to prepare the method for polyimide flexible copper-clad plate.Resulting polyimide flexible copper-clad plate is when having the excellent comprehensive performance, and its temperature tolerance significantly promotes, and particularly the bath temperature of anti-the soldering can reach 365 ℃.
Researchist of the present invention finds, obtain the better polyimide flexible copper-clad plate of heat resistance, can utilize bismaleimides and aromatic diamine to react, make the terpolymer BDME that dissolves in the low boiling point solvent with the Resins, epoxy reaction again, as the heat resistance modified component of Resins, epoxy; Consider that simultaneously bi-maleimide modified epoxy-resin systems fragility is big, the multipolymer EC that adds liquid nbr carboxyl terminal (CTBN) and Resins, epoxy therein utilizes BDME, EC and epoxy blend to obtain a kind of flexible copper-clad plate novel, that have excellent high temperature resistance character then and sticks with glue agent to improve its toughness.The quality proportioning of each component is as follows in this tackiness agent:
40～80 parts of bismaleimides multipolymers;
20～30 parts of liquid rubber modified epoxy resins;
20～100 parts of unmodified epoxy resins;
0～90 part of filler;
2～23 parts in solidifying agent.
Solid ingredient is dissolved in the organic solvent, and organic solvent is that acetone and butanone mix the mixed solvent that obtain by mass parts at 3: 2, and the solid content of whole system is 30%.
Wherein used bismaleimides multipolymer BDME is obtained by bismaleimides and aromatic diamine and Resins, epoxy copolymerization, wherein used bismaleimides is N, phenyl-bismaleimide between N-(PBMI) or N, phenyl-bismaleimide mixes the mixture that obtains according to a certain percentage with diphenyl methane dimaleimide (BMI) between N-, aromatic diamine is 4,4-diaminodiphenyl oxide (DDE), 4,4-diaminodiphenylsulfone(DDS) (DDS) or 4,4-diaminodiphenylmethane (DDM), the used Resins, epoxy of BDME is bisphenol A type epoxy resin.
Wherein used liquid rubber modified epoxy resin EC is obtained by Resins, epoxy and liquid nbr carboxyl terminal (CTBN) copolymerization.Wherein the mass content of the vinyl cyanide that contains among the CTBN is between 12～30%.The used Resins, epoxy of EC is bisphenol A type epoxy resin.
The unmodified epoxy resin of using in the prescription is in bisphenol A type epoxy resin, Racemic glycidol ether type epoxy, novolac epoxy, the phosphorous epoxy resin a kind or 2 kinds mixture wherein.
Used filler is a kind or wherein several mixture in talcum powder, silicon-dioxide, the titanium dioxide.Mainly be in order to improve the dimensional stability of gained flexible copper-clad plate.
Used solidifying agent is by 4,4-diaminodiphenyl oxide (DDE) was formed according to mass ratio with imidazole curing agent in 10: 1～1: 1, wherein imidazole curing agent is glyoxal ethyline and epoxy propane butyl ether affixture (704 solidifying agent) or glyoxal ethyline and vinyl cyanide affixture (781 solidifying agent) or 2, in the 4-methylimidazole a kind.
The step of preparation tackiness agent provided by the invention is as follows:
1) in taking back the stream and the reactor of inflated with nitrogen with bismaleimides, aromatic diamine and Resins, epoxy in 50～80 ℃ of following constant temperature stirring reactions 2～7 hours, reduce to room temperature, obtain bismaleimides multipolymer BDME;
2) in taking back the reactor of stream, with Resins, epoxy and nbr carboxyl terminal in 60～100 ℃ of following constant temperature stirring reactions 0.5～5 hour; Be warming up to 160 ℃, reacted 1～3 hour, reduce to room temperature, obtain liquid rubber modified epoxy resin EC.
3) BDME, EC and unmodified Resins, epoxy are added in the organic solvent, mixed at room temperature stirred 30 minutes, added filler, solidifying agent restir 30 minutes.
After leaving standstill froth breaking, obtain preparing the used tackiness agent of flexible copper-clad plate.
Using the method that above-mentioned tackiness agent provided by the invention prepares three-layer process polyimide flexible copper-clad plate is: tackiness agent is coated on the thick polyimide of 0.025～0.080mm (PI) film, subsequently that film is following dry 1～5 minute at 150 ℃, with the compound back of the thick Copper Foil of 0.010～0.030mm 160～165 ℃, the condition laminated of 2.0-3.0MPa, and under 150,180 and 210 ℃, respectively solidify and obtained polyimide flexible copper-clad plate (FCCL) product in 3 hours.
The invention provides a kind of span and come acid amides imines and the combined modified epoxyn of liquid nbr carboxyl terminal.Bismaleimides copolymer component wherein dissolves in the lower boiling ketones solvent, and has played the stable on heating effect of raising system, and rubber modified epoxy resin component has wherein played the effect toughness reinforcing to system.Polyimide flexible copper-clad plate with tackiness agent preparation provided by the present invention has significantly improved resistance toheat when having better comprehensive performance.
Embodiment
Embodiments of the invention are described in detail as follows.The present invention is confined to scope of embodiments.
Embodiment one:
The composition of modified epoxide resin adhesive and mass fraction:
5 parts of BDME;
20 parts of EC;
75 parts of bisphenol A type epoxy resins;
5 parts of talcum powder;
30 parts of DDE;
5 parts in 704 solidifying agent.
The detailed composition (massfraction) of BDME in this example: PBMI 12%; BMI12%; DDE 20%; Bisphenol A type epoxy resin 56%; The detailed composition (massfraction) of EC: CTBN (the vinyl cyanide mass content is 25% among the CTBN) 30%; Bisphenol A type epoxy resin 70%.
Solid ingredient is dissolved in the organic solvent, and organic solvent is that acetone and butanone mix the mixed solvent that obtain by mass parts at 3: 2, and the solid content of whole system is 30%.
The compound method of tackiness agent is:
1) in taking back the stream and the reactor of inflated with nitrogen with PBMI, BMI, DDE and bisphenol A type epoxy resin are reduced to room temperature in 70 ℃ of following constant temperature stirring reactions 2 hours, obtain bismaleimides multipolymer (being labeled as BDME1);
2) in taking back the reactor of stream, bisphenol A type epoxy resin and nbr carboxyl terminal CTBN in 80 ℃ of following constant temperature stirring reactions 1 hour, are warming up to 160 ℃, reacted 2 hours, reduce to room temperature, obtain liquid rubber modified epoxy resin (being labeled as EC1).
3) BDME1 and EC1, bisphenol A epoxide resin are added in the organic solvent, mixed at room temperature stirred 30 minutes, added filler, solidifying agent restir 30 minutes.After leave standstill froth breaking, stick with glue agent thereby obtain flexible copper-clad plate.
Tackiness agent is coated in (the gluing thickness that records is 0.021mm) on the thick polyimide of 0.025mm (PI) film, subsequently that film is following dry 3 minutes at 150 ℃, with the compound back of the thick Copper Foil of 0.018mm 165 ℃, the condition laminated of 2.4MPa, and under 150,180 and 210 ℃, respectively solidify and obtained polyimide flexible copper-clad panel products in 3 hours.
Embodiment two:
The composition of modified epoxide resin adhesive and mass fraction:
20 parts of BDME;
20 parts of EC;
60 parts of bisphenol A type epoxy resins;
5 parts of talcum powder;
27.5 parts of DDE;
7 parts in 704 solidifying agent;
The composition of BDME and EC is identical with embodiment one in this example.
Solid ingredient is dissolved in the organic solvent, and organic solvent is that acetone and butanone mix the mixed solvent that obtain by mass parts at 3: 2, and the solid content of whole system is 30%.
The compound method of tackiness agent and to prepare the method for polyimide flexible copper-clad plate identical with embodiment one.When the tackiness agent that uses this example to prepare prepared flexible copper-clad plate, used Kapton thickness was 0.025mm, and copper thickness is 0.018mm, gluing thickness 0.020mm.
Embodiment three:
The composition of modified epoxide resin adhesive and mass fraction:
20 parts of BDME;
20 parts of EC;
60 parts of bisphenol A type epoxy resins;
5 parts of talcum powder;
30 parts of DDE;
5 parts in 781 solidifying agent;
BDME's consists of (massfraction): PBMI 24% in this example; DDM 20%; Bisphenol A type epoxy resin 56%.And the composition of EC is identical with embodiment one.
Solid ingredient is dissolved in the organic solvent, and organic solvent is that acetone and butanone mix the mixed solvent that obtain by mass parts at 3: 2, and the solid content of whole system is 30%.
The compound method of tackiness agent is:
1) in taking back the stream and the reactor of inflated with nitrogen with PBMI, DDM and bisphenol A type epoxy resin in 80 ℃ of following constant temperature stirring reactions 3.5 hours, reduce to room temperature, obtain bismaleimides multipolymer (being labeled as BDME3).
2 in taking back the reactor of stream, and bisphenol A type epoxy resin and liquid nbr carboxyl terminal in 100 ℃ of following constant temperature stirring reactions 1 hour, are warming up to 160 ℃, reacted 2 hours, reduces to room temperature, obtains liquid rubber modified epoxy resin (being labeled as EC3).
3) BDME3 and EC3, bisphenol A epoxide resin are added in the organic solvent, mixed at room temperature stirred 30 minutes, added filler, solidifying agent restir 30 minutes.Leave standstill froth breaking, stick with glue agent thereby obtain flexible copper-clad plate.
It is identical with embodiment one to use the tackiness agent of this routine gained to prepare the method for polyimide flexible copper-clad plate.When the tackiness agent that uses this example to prepare prepared flexible copper-clad plate, used Kapton thickness was 0.025mm, and copper thickness is 0.018mm, gluing thickness 0.020mm.
Embodiment four:
The composition of modified epoxide resin adhesive and mass fraction:
5 parts of BDME;
35 parts of EC;
60 parts of bisphenol A type epoxy resins;
10 parts of Racemic glycidol ether type epoxies;
8 parts of titanium dioxide;
30 parts of DDE;
6 parts in 781 solidifying agent;
The composition of BDME and EC is identical with embodiment one in this example.
Solid ingredient is dissolved in the organic solvent, and organic solvent is that acetone and butanone mix the mixed solvent that obtain by mass parts at 3: 2, and the solid content of whole system is 30%.
The compound method of tackiness agent and to prepare the method for polyimide flexible copper-clad plate identical with embodiment one.When the tackiness agent that uses this example to prepare prepared flexible copper-clad plate, used Kapton thickness was 0.025mm, and copper thickness is 0.018mm, gluing thickness 0.022mm.
Embodiment five:
The composition of modified epoxide resin adhesive and mass fraction:
20 parts of BDME;
20 parts of EC;
100 parts of bisphenol A type epoxy resins;
7 parts of silicon-dioxide;
14 parts of DDE;
8 parts in 704 solidifying agent;
In this example, the composition of BDME is identical with embodiment one.The composition of EC (massfraction) is: CTBN (the vinyl cyanide mass content is 12% among the CTBN) 30%; Bisphenol A type epoxy resin 70%.
Solid ingredient is dissolved in the organic solvent, and organic solvent is that acetone and butanone mix the mixed solvent that obtain by mass parts at 3: 2, and the solid content of whole system is 30%.
The compound method of tackiness agent and to prepare the method for polyimide flexible copper-clad plate identical with embodiment one.When the tackiness agent that uses this example to prepare prepared flexible copper-clad plate, used Kapton thickness was 0.025mm, and copper thickness is 0.018mm, gluing thickness 0.020mm.
Embodiment six:
The composition of modified epoxide resin adhesive and mass fraction:
20 parts of BDME;
20 parts of EC;
30 parts of bisphenol A type epoxy resins;
30 parts of phosphorous epoxy resins;
5 parts of talcum powder;
30 parts of DDE
5.5 parts in 704 solidifying agent
In this example, the composition of BDME and EC is identical with embodiment one.
Solid ingredient is dissolved in the organic solvent, and organic solvent is that acetone and butanone mix the mixed solvent that obtain by mass parts at 3: 2, and the solid content of whole system is 30%.
The compound method of tackiness agent and to prepare the method for polyimide flexible copper-clad plate identical with embodiment one.When the tackiness agent that uses this example to prepare prepared flexible copper-clad plate, used Kapton thickness was 0.025mm, and copper thickness is 0.018mm, gluing thickness 0.019mm.
Embodiment seven:
The composition of modified epoxide resin adhesive and mass fraction:
20 parts of BDME;
20 parts of EC;
30 parts of bisphenol A type epoxy resins;
45 parts of phosphorous epoxy resins;
5 parts of titanium dioxide;
30 parts of DDE
7 parts in 704 solidifying agent
In this example, the composition of BDME and EC is identical with embodiment one.
Solid ingredient is dissolved in the organic solvent, and organic solvent is that acetone and butanone mix the mixed solvent that obtain by mass parts at 3: 2, and the solid content of whole system is 30%.
The compound method of tackiness agent is:
1) in taking back the stream and the reactor of inflated with nitrogen with PBMI, DDE and bisphenol A type epoxy resin in 70 ℃ of following constant temperature stirring reactions 3 hours, reduce to room temperature, obtain bismaleimides multipolymer (being labeled as BDME7).
2 in taking back the reactor of stream, and bisphenol A type epoxy resin and liquid nbr carboxyl terminal in 90 ℃ of following constant temperature stirring reactions 1 hour, are warming up to 160 ℃, reacted 2 hours, reduces to room temperature, obtains liquid rubber modified epoxy resin (being labeled as EC7).
3) BDME7 and EC7, bisphenol A epoxide resin and phosphorous epoxy resin are added in the organic solvent, mixed at room temperature stirred 30 minutes, added filler, solidifying agent restir 30 minutes.Leave standstill froth breaking, stick with glue agent thereby obtain flexible copper-clad plate.
The method that the tackiness agent that uses this example to provide prepares the polyimide flexible copper-clad plate is identical with embodiment one.In this example, used Kapton thickness is 0.025mm, and copper thickness is 0.018mm, gluing thickness 0.021mm.
The performance of each embodiment gained polyimide flexible copper-clad plate is as shown in table 1.
The over-all properties of the different embodiment gained of table 1 flexible copper-clad plate
Annotate: the folding resistance in the testing method carries out according to the standard of JIS C5016-19948.7, and other test events are carried out according to the methods involving among the IPC-TM-650-2.
Claims (9)
1. a span comes acid amides imines and the combined modified epoxyn composition of liquid nbr carboxyl terminal, it is characterized in that, is made up of solid ingredient and organic solvent, and solid ingredient comprises (calculating by mass parts):
40～80 parts of bismaleimides multipolymers;
20～30 parts of liquid rubber modified epoxy resins;
20～100 parts of unmodified epoxy resins;
0～90 part of filler;
2～23 parts in solidifying agent
Solid ingredient is dissolved in the organic solvent, and organic solvent is that acetone and butanone mix the mixed solvent that obtain by mass parts at 3: 2, and the solid content of whole system is 30%.
2. bismaleimides multipolymer as claimed in claim 1, it is characterized in that, this bismaleimides multipolymer is to be obtained by bismaleimides, aromatic diamine and Resins, epoxy copolymerization, and wherein bismaleimides is N, phenyl-bismaleimide between N-(PBMI), or mix the mixture that obtains by a certain percentage with diphenyl methane dimaleimide (BMI), aromatic diamine is 4,4-diaminodiphenyl oxide (DDE), or 4,4-diaminodiphenylmethane (DDM), used Resins, epoxy are bisphenol A type epoxy resin.
3. liquid rubber modified epoxy resin as claimed in claim 1, it is characterized in that, it is the multipolymer of liquid nbr carboxyl terminal (CTBN) and Resins, epoxy, the mass content of the vinyl cyanide that contains among the wherein used CTBN is between 12～30%, and used Resins, epoxy is bisphenol A type epoxy resin.
4. unmodified epoxy resin as claimed in claim 1 is characterized by, and used Resins, epoxy is in bisphenol A type epoxy resin, Racemic glycidol ether type epoxy, novolac epoxy, the phosphorous epoxy resin a kind or 2 kinds mixture wherein.
5. filler as claimed in claim 1 is characterized in that, this filler is in talcum powder, silicon-dioxide and the titanium dioxide a kind or several.
6. solidifying agent as claimed in claim 1 is characterized in that this solidifying agent is made up of diaminodiphenyl oxide and imidazole curing agent, and its mass ratio is 10: 1～1: 1.
7. imidazole curing agent as claimed in claim 6, it is characterized in that, this solidifying agent is glyoxal ethyline and epoxy propane butyl ether affixture (704 solidifying agent) or glyoxal ethyline and vinyl cyanide affixture (781 solidifying agent) or 2, in the 4-methylimidazole a kind.
8. one kind prepares the method that span comes the combined modified epoxyn of acid amides imines and liquid nbr carboxyl terminal, it is characterized in that, is made up of following steps:
1) in taking back the stream and the reactor of inflated with nitrogen with bismaleimides, aromatic diamine and Resins, epoxy in 50～80 ℃ of following constant temperature stirring reactions 2～7 hours, reduce to room temperature, obtain bismaleimides multipolymer (BDME);
2) in taking back the reactor of stream, Resins, epoxy and nbr carboxyl terminal in 60～100 ℃ of following constant temperature stirring reactions 0.5～5 hour, are warming up to 160 ℃, reacted 1～3 hour, reduce to room temperature, obtain liquid rubber modified epoxy resin (EC);
3) BDME, EC and unmodified Resins, epoxy are added in the organic solvent, mixed at room temperature stirred 30 minutes, added filler, solidifying agent restir 30 minutes;
After leaving standstill froth breaking, obtain preparing the used tackiness agent of polyimide flexible copper-clad plate.
9. the modified epoxide resin adhesive that uses claim 8 to prepare prepares the method for polyimide flexible copper-clad plate: tackiness agent is coated on the thick polyimide of 0.025～0.080mm (PI) film, subsequently that film is following dry 1～5 minute at 150 ℃, with the compound back of the thick Copper Foil of 0.010～0.030mm 160～165 ℃, the condition laminated of 2.0-3.0MPa, and under 150,180 and 210 ℃, respectively solidify and obtained polyimide flexible copper-clad plate (FCCL) product in 3 hours.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2011100809120A CN102199413A (en) | 2011-03-26 | 2011-03-26 | Modified epoxy resin adhesive used for polyimide flexible copper-clad plate |
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| Application Number | Priority Date | Filing Date | Title |
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| CN2011100809120A CN102199413A (en) | 2011-03-26 | 2011-03-26 | Modified epoxy resin adhesive used for polyimide flexible copper-clad plate |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102936468A (en) * | 2012-11-28 | 2013-02-20 | 九江福莱克斯有限公司 | Flame-retardant epoxy resin adhesive and flexible copper-clad plate made by using same |
| CN103214793A (en) * | 2013-04-22 | 2013-07-24 | 东华大学 | Advanced composite material matrix resin and preparation method thereof |
| CN105441003A (en) * | 2016-01-05 | 2016-03-30 | 济南北方泰和新材料有限公司 | Epoxy resin adhesive and preparation method thereof |
| CN105473657A (en) * | 2013-09-30 | 2016-04-06 | 汉高知识产权控股有限责任公司 | Conductive die attach film for large die semiconductor packages and compositions useful for the preparation thereof |
| CN107487034A (en) * | 2017-08-23 | 2017-12-19 | 熊秀 | A kind of lightning protection wire netting composite membrane and preparation method thereof |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102936468A (en) * | 2012-11-28 | 2013-02-20 | 九江福莱克斯有限公司 | Flame-retardant epoxy resin adhesive and flexible copper-clad plate made by using same |
| CN103214793A (en) * | 2013-04-22 | 2013-07-24 | 东华大学 | Advanced composite material matrix resin and preparation method thereof |
| CN105473657A (en) * | 2013-09-30 | 2016-04-06 | 汉高知识产权控股有限责任公司 | Conductive die attach film for large die semiconductor packages and compositions useful for the preparation thereof |
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| CN105473657B (en) * | 2013-09-30 | 2017-12-22 | 汉高知识产权控股有限责任公司 | Composition for the conductive wafer adhesive film of larger wafers package semiconductor and for preparing conductive wafer adhesive film |
| CN105441003A (en) * | 2016-01-05 | 2016-03-30 | 济南北方泰和新材料有限公司 | Epoxy resin adhesive and preparation method thereof |
| CN107487034A (en) * | 2017-08-23 | 2017-12-19 | 熊秀 | A kind of lightning protection wire netting composite membrane and preparation method thereof |
| CN107487034B (en) * | 2017-08-23 | 2020-05-08 | 范晓宇 | Lightning protection metal mesh composite film and preparation method thereof |
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Application publication date: 20110928 |