CN114656893A - Low dielectric adhesive film material based on maleic anhydride functionalized styrene-butadiene rubber and application thereof - Google Patents
Low dielectric adhesive film material based on maleic anhydride functionalized styrene-butadiene rubber and application thereof Download PDFInfo
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- CN114656893A CN114656893A CN202210172140.1A CN202210172140A CN114656893A CN 114656893 A CN114656893 A CN 114656893A CN 202210172140 A CN202210172140 A CN 202210172140A CN 114656893 A CN114656893 A CN 114656893A
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- maleic anhydride
- butadiene rubber
- anhydride functionalized
- functionalized styrene
- low dielectric
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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
- C09J7/00—Adhesives in the form of films or foils
- C09J7/30—Adhesives in the form of films or foils characterised by the adhesive composition
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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
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J153/02—Vinyl aromatic monomers and conjugated dienes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
-
- 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
- C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
- C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
Abstract
The invention relates to a low dielectric adhesive film material based on maleic anhydride functionalized styrene-butadiene rubber and application thereof. The composition is prepared from the following components in percentage by weight: 60-90% of styrene butadiene copolymer, 5-35% of maleic anhydride functionalized styrene-butadiene rubber, 1-3% of epoxy resin, 1-3% of cross-linking agent and 1-3% of initiator. Compared with the prior art, the adhesive film provided by the invention takes the styrene block copolymer as a matrix, and the epoxy resin and the maleic anhydride functionalized styrene-butadiene rubber are added as modified materials. The epoxy resin and the unsaturated addition polymer containing double bonds have excellent dielectric properties, good mechanical properties and excellent heat resistance and adhesiveness. The adhesive film can be widely applied to the fields of FPC and PCB.
Description
Technical Field
The invention belongs to the technical field of dielectric adhesive film materials, and particularly relates to a low dielectric adhesive film material based on maleic anhydride functionalized styrene-butadiene rubber and application thereof.
Background
With the continuous development of the IT industry and the upcoming 5G/6G industry, the demand for such highly information-oriented industries has increased greatly, and the high frequency of electronic devices has become a development trend in the present society. Especially, the rapid development of the communication industry, the popularization of wireless devices, and the development of high frequency FPCs (flexible circuit boards) and PCBs (printed circuit boards) are of great importance.
In the development of high frequency of FPC and PCB materials, not only the substrate is required to have low dielectric characteristics, but also the weatherability and performance stability of the material are important aspects. The material prepared by the traditional adhesive has high dielectric constant and poor heat resistance and weather resistance, and further causes high dielectric loss, difficult processing and short service life.
How to invent an adhesive product to enable the prepared FPC and PCB products to have the characteristics of low dielectric constant, high heat resistance, excellent toughness and the like is a problem to be solved urgently at present.
Disclosure of Invention
Aiming at the current situation that FPC or PCB products with low dielectric constant, high heat resistance and excellent toughness are lacked in the prior art, the invention provides a low dielectric adhesive film material based on maleic anhydride functionalized styrene-butadiene rubber and application thereof.
The high-frequency material prepared by the low dielectric adhesive film material based on maleic anhydride functionalized styrene-butadiene rubber provided by the invention has the characteristics of low dielectric constant, high heat resistance, excellent toughness and the like.
The purpose of the invention can be realized by the following technical scheme:
the invention provides a low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber, which is prepared from the following components in percentage by weight:
the maleic anhydride functionalized styrene-butadiene rubber is formed by grafting maleic anhydride molecules on a styrene-butadiene copolymer, and the molecular formula is shown as follows, wherein the vinyl content of the maleic anhydride functionalized styrene-butadiene rubber is between 20% and 60%, and the maleic anhydride functional group content of the maleic anhydride functionalized styrene-butadiene rubber is between 2 molecules per molecular chain and 20 molecules per molecular chain.
In one embodiment of the invention, the styrene butadiene copolymer has a vinyl content of between 20% and 90%, preferably a vinyl content of between 50% and 90%.
In one embodiment of the invention, the styrene butadiene copolymer has a molecular weight (Mn) between 2000 and 10000, preferably between 2500 and 6000.
In one embodiment of the invention, the maleic anhydride functionalized styrene butadiene rubber has a molecular weight (Mn) between 3000 and 10000, preferably a molecular weight (Mn) between 5000 and 10000.
In one embodiment of the invention, the maleic anhydride functionalized styrene-butadiene rubber has a vinyl content of between 20% and 35%.
In one embodiment of the invention, the maleic anhydride functionalized styrene-butadiene rubber has a maleic anhydride functional group content of between 6 and 17 per molecular chain.
In one embodiment of the present invention, the epoxy resin is selected from organic high molecular compounds having two or more epoxy groups in the molecule, and bisphenol a type epoxy resins are preferred.
In one embodiment of the present invention, the crosslinking agent is selected from one or more of tri (allyl) isocyanate (TMAIC), triallyl isocyanurate (TAIC) and triallyl cyanurate (TAC).
In one embodiment of the invention, the initiator is selected from organic peroxy-type initiators; the organic peroxy initiator comprises dialkyl peroxide, hydroperoxide, peroxyester and diacyl peroxide; one or more peroxydicarbonates, preferably dialkyl peroxides or hydroperoxides,
the dialkyl peroxide is selected from di-tert-butyl peroxide or dicumyl peroxide; the hydroperoxide is selected from cumene hydroperoxide or tert-butyl hydroperoxide.
Preferably, in one embodiment of the invention, the initiator is selected from dicumyl peroxide (DCP) or di- (tert-butylperoxyisopropyl) benzene (BIBP).
The invention also provides a preparation method of the low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber, which comprises the following steps:
(1) adding styrene butadiene copolymer, maleic anhydride functionalized styrene-butadiene rubber, epoxy resin, a cross-linking agent and an initiator into a solvent, mechanically stirring, and forming transparent glue solution with certain viscosity after stirring;
(2) and coating the obtained glue solution on a material through a coating machine, drying and drying the solvent through hot air after the glue solution is leveled, and obtaining the low dielectric film material based on the maleic anhydride functionalized styrene-butadiene rubber.
In one embodiment of the present invention, in step (1), the solvent is an organic solvent, and is selected from toluene, xylene, cyclohexane, chloroform, methyl ethyl ketone, cyclohexanone or solvent oil, or a mixture of two or more thereof.
In one embodiment of the present invention, in the step (2), the temperature of the hot wind is 60 to 140 ℃, preferably 60 to 80 ℃.
The invention also provides an application of the low dielectric adhesive film material based on the maleic anhydride functionalized styrene-butadiene rubber, and the low dielectric adhesive film material based on the maleic anhydride functionalized styrene-butadiene rubber is used for preparing a high-frequency FPC or a high-frequency PCB.
The adhesive film provided by the invention takes a styrene block copolymer as a matrix, and epoxy resin and maleic anhydride functionalized styrene-butadiene rubber are added as modified materials. The adhesive film disclosed by the invention has excellent dielectric property, good mechanical property and excellent heat resistance and adhesiveness.
Compared with the prior art, the invention has the following advantages and beneficial effects:
1. the traditional adhesive has higher dielectric constant, is suitable for low-end electronic equipment, but is not suitable for high-frequency products; the main component of the adhesive film material is styrene butadiene copolymer with low dielectric constant and low loss, so the adhesive film material is suitable for high-frequency FPC or high-frequency PCB.
2. The heat resistance is high. The traditional adhesive has a large heat resistance problem because a large amount of acrylate, epoxy resin and the like are generally used, and the main component of the adhesive is the crosslinkable styrene-butadiene copolymer, so that the crosslinked styrene-butadiene copolymer has extremely high glass transition temperature and good heat resistance.
Detailed Description
The present invention is further illustrated by the following examples, but the scope of the present invention is not limited to these examples. Other variations and modifications which may occur to those skilled in the art without departing from the spirit and scope of the invention are intended to be included within the scope of the invention.
Example 1
The preparation method of the low dielectric adhesive film comprises the following specific steps:
(1) according to the dosage of the table 1, adding styrene butadiene copolymer, maleic anhydride functionalized styrene-butadiene rubber, trimethyl allyl isocyanate, epoxy resin and bis (tert-butylperoxy) p-diisopropylbenzene initiator into toluene solvent, mechanically stirring for 1000r/min, and stirring for 10min to form transparent glue solution with certain viscosity;
(2) and (3) coating the glue solution on a copper foil through a coating machine, standing for 5min until the glue solution is leveled, and then drying in a forced air drying oven at 80 ℃ for 5min to obtain the copper foil with the glue, wherein the thickness of the glue layer on the copper foil is 25 microns.
In this example, the styrene butadiene copolymer was Ricon100 available from CRAY VALLEY, the vinyl content was 70%, and the number average molecular weight (Mn) was 4500
In this example, the maleic anhydride functionalized styrene-butadiene rubber is Ricon184MA6 manufactured by CRAY VALLEY company, the vinyl content is 20% -40%, the number average molecular weight (Mn) is 9900, and the content of maleic anhydride functional groups is 6 per molecular chain.
In this example, the epoxy resin is E51.
In this example, the crosslinker is TAC.
In this example, the initiator is BIBP.
And (3) testing:
putting the dried copper foil with the adhesive film into a nitrogen oven to cure the adhesive film at 180 ℃ for 60 min; removing copper foil by etching to obtain transparent adhesive film with no wrinkle on surface, cleaning with deionized water twice, drying in 80 deg.C air-blast drying oven for 2 hr, standing in drying dish for 10min, and testing dielectric property of the adhesive film according to standard IPC-TM-6502.5.5, wherein the dielectric constant is 2.56 and dielectric loss is 1.73 x 10-3(ii) a The water absorption of the adhesive film is tested according to the standard IPC-TM-6502.6.2.1, and the water absorption is 0.6%.
Example 2
The preparation method of the low dielectric adhesive film comprises the following specific steps:
(1) according to the table 1, adding a styrene butadiene copolymer, maleic anhydride functionalized styrene-butadiene rubber, trimethyl allyl isocyanate, epoxy resin and a bis (tert-butylperoxy) p-diisopropylbenzene initiator into a xylene solvent, mechanically stirring for 1000r/min, and stirring for 10min to form a transparent glue solution with certain viscosity;
(2) coating the glue solution on a PET release film through a coating machine, standing for 5min until the glue solution is leveled, drying in an air drying oven at 80 ℃ for 5min, drying the solvent, and then covering a layer of release paper on the surface. Thus obtaining the pure adhesive film clamped between the release film and the release paper, wherein the thickness of the adhesive film is 20 microns.
In this example, the styrene butadiene copolymer was Ricon181 available from CRAY VALLEY, having a vinyl content of 20% to 40%, and a number average molecular weight (Mn) of 3200
In this example, the maleic anhydride functionalized styrene-butadiene rubber is Ricon184MA6 manufactured by CRAY VALLEY company, the vinyl content is 20% -40%, the number average molecular weight (Mn) is 9900, and the content of maleic anhydride functional groups is 6 per molecular chain.
In this example, the epoxy resin is E51.
In this example, the crosslinker is TAIC.
In this example, the initiator is DCP.
And (3) testing:
and stripping the release paper on the surface of the pure adhesive film, then pasting the adhesive film on the polyimide film, removing the PET release film on the other side, then covering a layer of electrolytic copper foil with rough surface on the adhesive film, laminating in a hot pressing mode, and bonding the electrolytic copper foil on the polyimide surface to obtain the polyimide plate with copper-coated surface. The hot pressing temperature is 190 ℃, the pressure is 2.4MPa, and the time is 70 min.
The hot-pressed sample was taken out and cut into test specimens 2cm wide and 8cm long, and the peel strength was measured according to IPC-TM-6502.4.8 standard to give a peel strength of 0.8N/mm.
The hot-pressed sample was taken out, cut into 5cm by 5cm squares to test the heat resistance of the sample, and dipped in tin for 10 seconds at 288 ℃ for 3 times in a tin furnace according to the IPC-TM-6502.4.13 standard without generating bubbles.
Examples 3 to 5
The preparation method of the low dielectric adhesive film comprises the following specific steps:
(1) according to the table 1, adding a styrene butadiene copolymer, maleic anhydride functionalized styrene-butadiene rubber, trimethyl allyl isocyanate, epoxy resin and a bis (tert-butylperoxy) p-diisopropylbenzene initiator into a toluene solvent, mechanically stirring for 1000r/min, and stirring for 10min to form a transparent glue solution with certain viscosity;
(2) coating the glue solution on a PET release film through a coating machine, standing for 5min until the glue solution is leveled, drying in an air drying oven at 80 ℃ for 5min, drying the solvent, and then covering a layer of release paper on the surface. Thus obtaining the pure adhesive film clamped between the release film and the release paper, wherein the thickness of the adhesive film is 20 microns.
In this example, the styrene butadiene copolymer was Ricon100 available from CRAY VALLEY, the vinyl content was 70%, and the number average molecular weight (Mn) was 4500.
In this example, the maleic anhydride functionalized styrene-butadiene rubber is Ricon184MA6 manufactured by CRAY VALLEY company, the vinyl content is 20% -40%, the number average molecular weight (Mn) is 9900, and the content of maleic anhydride functional groups is 6 per molecular chain.
In this example, the epoxy resin is E51.
In this example, the crosslinker was TAIC.
In this example, the initiator was DCP.
And (3) testing:
and (3) stripping the release paper on the surface of the pure adhesive film obtained in the embodiment 3, then pasting the adhesive film on the polyimide film, removing the PET release film on the other side, then covering a layer of electrolytic copper foil with a rough surface on the adhesive film, laminating in a hot pressing mode, and bonding the electrolytic copper foil on the polyimide surface to obtain the polyimide plate with the copper-clad surface. The hot pressing temperature is 180 ℃, the pressure is 2MPa, and the time is 80 min.
The hot-pressed sample was taken out, cut into test specimens having a width of 2cm and a length of 8cm, and tested for peel strength according to IPC-TM-6502.4.8 standard to give a peel strength of 0.9N/mm.
The hot-pressed sample was taken out, cut into 5cm by 5cm squares to test the heat resistance of the sample, and dipped in tin for 10 seconds at 288 ℃ for 3 times in a tin furnace according to the IPC-TM-6502.4.13 standard without generating bubbles.
Taking out the hot-pressed sample, removing the copper foil by etching to obtain a transparent modified polyimide film without wrinkles on the surface, cleaning twice with deionized water, then drying in a forced air drying oven at 80 ℃ for 2h, finally standing in a drying dish for 10min, and testing the dielectric property of the adhesive film according to the standard IPC-TM-6502.5.5, wherein the dielectric constant is 3.31 and the dielectric loss is 2.52 to 10-3(ii) a The water absorption of the adhesive film was measured according to the standard IPC-TM-6502.6.2.1 and was 0.7%.
TABLE 1 amounts of the components used in the different examples
The embodiments described above are described to facilitate an understanding and use of the invention by those skilled in the art. It will be readily apparent to those skilled in the art that various modifications to these embodiments may be made, and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present invention is not limited to the above embodiments, and those skilled in the art should make improvements and modifications within the scope of the present invention based on the disclosure of the present invention.
Claims (10)
1. A low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber is characterized by being prepared from the following components in percentage by weight:
the vinyl content of the maleic anhydride functionalized styrene-butadiene rubber is between 20% and 60%, and the maleic anhydride functional group content of the maleic anhydride functionalized styrene-butadiene rubber is between 2/molecular chain and 20/molecular chain.
2. The low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber according to claim 1, wherein the vinyl content of the styrene-butadiene copolymer is between 20% and 90%, preferably the vinyl content is between 50% and 90%;
the styrene butadiene copolymer has a molecular weight (Mn) between 2000 and 10000, preferably between 2500 and 6000.
3. A low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber according to claim 1, characterized in that the molecular weight (Mn) of the maleic anhydride functionalized styrene-butadiene rubber is between 3000 and 10000, preferably between 5000 and 10000.
4. The low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber of claim 1, wherein the vinyl content of the maleic anhydride functionalized styrene-butadiene rubber is between 20% and 35%, and the maleic anhydride functional group content of the maleic anhydride functionalized styrene-butadiene rubber is between 6 molecules/molecule chain and 17 molecules/molecule chain.
5. The low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber according to claim 1, wherein the epoxy resin is selected from organic high molecular compounds containing two or more epoxy groups in the molecule, preferably bisphenol A epoxy resin.
6. The low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber as claimed in claim 1, wherein the crosslinking agent is selected from one or more of tri allyl isocyanate, triallyl isocyanurate or triallyl cyanurate.
7. The low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber according to claim 1, wherein the initiator is selected from organic peroxy initiators; the organic peroxy initiator comprises dialkyl peroxide, hydroperoxide, peroxyester and diacyl peroxide; one or more peroxydicarbonates, preferably dialkyl peroxides or hydroperoxides,
the dialkyl peroxide is selected from di-tert-butyl peroxide or dicumyl peroxide; the hydroperoxide is selected from cumene hydroperoxide or tert-butyl hydroperoxide.
8. The preparation method of the low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber of any one of claims 1 to 7, characterized by comprising the following steps:
(1) adding styrene butadiene copolymer, maleic anhydride functionalized styrene-butadiene rubber, epoxy resin, a cross-linking agent and an initiator into a solvent, mechanically stirring, and forming transparent glue solution with certain viscosity after stirring;
(2) and coating the obtained glue solution on a material through a coating machine, drying and drying the solvent through hot air after the glue solution is leveled, and obtaining the low dielectric film material based on the maleic anhydride functionalized styrene butadiene rubber.
9. The method for preparing a low dielectric film material based on maleic anhydride functionalized styrene-butadiene rubber according to claim 8, wherein in the step (1), the solvent is an organic solvent, and a single solvent or a mixed solvent of two or more of toluene, xylene, cyclohexane, chloroform, methyl ethyl ketone, cyclohexanone and solvent oil is selected;
in the step (2), the temperature of the hot air is 60-140 ℃, preferably 60-80 ℃.
10. Use of the maleic anhydride functionalized styrene-butadiene rubber based low dielectric adhesive film material according to any one of claims 1 to 8, wherein the maleic anhydride functionalized styrene-butadiene rubber based low dielectric adhesive film material is used for preparing a high frequency FPC or a high frequency PCB.
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| CN202210172140.1A CN114656893A (en) | 2022-02-24 | 2022-02-24 | Low dielectric adhesive film material based on maleic anhydride functionalized styrene-butadiene rubber and application thereof |
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| CN202210172140.1A CN114656893A (en) | 2022-02-24 | 2022-02-24 | Low dielectric adhesive film material based on maleic anhydride functionalized styrene-butadiene rubber and application thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5569545A (en) * | 1993-12-28 | 1996-10-29 | Nippon Denkai Ltd. | Copper clad laminate, multilayer printed circuit board and their processing method |
| CN110317445A (en) * | 2019-07-22 | 2019-10-11 | 南亚新材料科技股份有限公司 | A kind of high frequency resin composition and its application |
| CN111378212A (en) * | 2018-12-29 | 2020-07-07 | 广东生益科技股份有限公司 | Resin composition, prepreg containing same and dielectric substrate for antenna |
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2022
- 2022-02-24 CN CN202210172140.1A patent/CN114656893A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5569545A (en) * | 1993-12-28 | 1996-10-29 | Nippon Denkai Ltd. | Copper clad laminate, multilayer printed circuit board and their processing method |
| CN111378212A (en) * | 2018-12-29 | 2020-07-07 | 广东生益科技股份有限公司 | Resin composition, prepreg containing same and dielectric substrate for antenna |
| CN110317445A (en) * | 2019-07-22 | 2019-10-11 | 南亚新材料科技股份有限公司 | A kind of high frequency resin composition and its application |
| KR20210090653A (en) * | 2019-07-22 | 2021-07-20 | 난야 뉴 머티리얼 테크놀로지 컴퍼니 리미티드 | High frequency resin composition and its application |
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