JPS63199219A - Resin composition for laminated board - Google Patents
Resin composition for laminated boardInfo
- Publication number
- JPS63199219A JPS63199219A JP3117787A JP3117787A JPS63199219A JP S63199219 A JPS63199219 A JP S63199219A JP 3117787 A JP3117787 A JP 3117787A JP 3117787 A JP3117787 A JP 3117787A JP S63199219 A JPS63199219 A JP S63199219A
- Authority
- JP
- Japan
- Prior art keywords
- butadiene polymer
- weight
- epoxidized
- tetrabromobisphenol
- parts
- 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
- 239000011342 resin composition Substances 0.000 title claims description 8
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 claims abstract description 23
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 abstract description 7
- -1 acrylic compound Chemical class 0.000 abstract description 7
- 229920002857 polybutadiene Polymers 0.000 abstract description 7
- 239000003054 catalyst Substances 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 230000009477 glass transition Effects 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- 150000002978 peroxides Chemical class 0.000 abstract description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000178 monomer Substances 0.000 abstract description 3
- 229920003986 novolac Polymers 0.000 abstract description 2
- 239000005011 phenolic resin Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract description 2
- 150000003512 tertiary amines Chemical class 0.000 abstract description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 11
- 239000002966 varnish Substances 0.000 description 8
- 239000004744 fabric Substances 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000000465 moulding Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229910000679 solder Inorganic materials 0.000 description 5
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000004745 nonwoven fabric Substances 0.000 description 4
- 238000011056 performance test Methods 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical class OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229920003319 Araldite® Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000010680 novolac-type phenolic resin Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229920006250 telechelic polymer Polymers 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
Abstract
Description
【発明の詳細な説明】
産業上の利用分野
本発明は電気特性、特に誘電特性にすぐれたガラス布、
紙等を基材として用いるプリント配線基板用の難燃化さ
れた積層板用樹脂組成物に関するものである。DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to glass cloth with excellent electrical properties, particularly dielectric properties,
The present invention relates to a resin composition for flame-retardant laminates for printed wiring boards using paper or the like as a base material.
従来の技術
最近、電子素子の高密度化、信号の高速化、高周波数化
に伴ない信号の遅延が問題となってきている。信号遅延
時間は、比誘導率の平方根に比例して大きくなるので高
速電子機器のプリント配線板は誘電率の低いものが求め
られている。最も広く用いられているガラス布を基材と
するエポキシ樹脂積層板は誘電率が４．５〜５とかなり
大きく高速電子機器用、高周波機器用としては不利であ
る。2. Description of the Related Art In recent years, signal delay has become a problem as electronic devices become denser, signal speeds become faster, and frequencies become higher. Since the signal delay time increases in proportion to the square root of the specific dielectric constant, printed wiring boards for high-speed electronic devices are required to have a low dielectric constant. The most widely used epoxy resin laminate based on glass cloth has a fairly large dielectric constant of 4.5 to 5, which is disadvantageous for use in high-speed electronic devices and high-frequency devices.
発明が解決しようとする問題点
誘電率の低いポリエチレン樹脂、テフロン樹脂、ポリフ
ェニレンオキサイド樹脂、ポリスルホン樹脂などを用い
た基板が開発されているが、これらは熱可盟性樹脂であ
るため、強度が小さいあるいははんだ、耐熱性などに問
題がある。Problems that the invention aims to solveSubstrates using polyethylene resin, Teflon resin, polyphenylene oxide resin, polysulfone resin, etc. with low dielectric constants have been developed, but since these are thermoplastic resins, their strength is low. Or there is a problem with solder, heat resistance, etc.
本発明者らは誘電率が低く、しかも熱硬化製樹脂である
１、２型の二重結合を５０％以上有するブタジェンの低
重合体について研究し、前にエポキシ化ポリブタジェン
をノボラック型フェノール樹脂あるいはポリビニルフェ
ノールで硬化させることにより、誘電率が低く、強度が
大きく、しかもはんだ耐熱性の優れた積層板が得られる
とを見出し特許を出願した（特開昭６０−８６１３４号
）上記の樹脂から製造された積層板は優れた性能を有し
ているが、燃焼し易いという問題があった。The present inventors researched a low dielectric constant of butadiene, which is a thermosetting resin and has 50% or more of type 1 and type 2 double bonds. He discovered that a laminate with low dielectric constant, high strength, and excellent solder heat resistance could be obtained by curing with polyvinylphenol, and filed a patent application (Japanese Patent Application Laid-Open No. 60-86134) for manufacturing from the above resin. Although the resulting laminate has excellent performance, it has the problem of being easily combustible.
本発明者らは難燃化について検討した結果、エポキシ化
ポリブタジェンをテトラブロモビスフェノールＡで硬化
させることにより、難燃性で誘電率が低く、強度が大き
く、しかもはんだ耐熱性の優れた積層板が得られること
を見出し特許を出願した（特願昭６１−１９２７２０号
）。The present inventors investigated flame retardancy and found that by curing epoxidized polybutadiene with tetrabromobisphenol A, a laminate with flame retardancy, low dielectric constant, high strength, and excellent soldering heat resistance was created. He discovered that it could be obtained and applied for a patent (Japanese Patent Application No. 192720/1982).
この場合、硬化剤が２官能であるため架橋密度が低いた
めか、ガラス転移温度が低く、しかも耐塩化メチレン性
が悪いという問題があった。In this case, there were problems in that the glass transition temperature was low and the methylene chloride resistance was poor, probably because the crosslinking density was low because the curing agent was difunctional.
本発明の目的は電気特性に優れ、架橋密度が高く、耐熱
性が優れ、しかも難燃性の優れた積層板用樹脂組成物を
提供することにある。An object of the present invention is to provide a resin composition for a laminate that has excellent electrical properties, high crosslinking density, excellent heat resistance, and excellent flame retardancy.
問題点を解決するための手段
本発明者らは種々研究した結果、エポキシ化ポリブタジ
ェンをテトラブロモビスフェノールＡおよび特定のアク
リル化合物で二種類の硬化形式で硬化させることにより
、ガラス転移温度が高く、耐塩化メチレン性が良く、難
燃性が優れ、誘電率が低く、強度が大きく、しかもはん
だ耐熱性の優れた積層板が得られることを見出し本発明
に到達した。Means for Solving the Problems As a result of various studies, the present inventors found that by curing epoxidized polybutadiene with tetrabromobisphenol A and a specific acrylic compound in two types of curing formats, it has a high glass transition temperature and is resistant. The present invention was achieved by discovering that a laminate with good methylene chloride properties, excellent flame retardancy, low dielectric constant, high strength, and excellent solder heat resistance can be obtained.
すなわち本発明は
（Ａ）５００〜５０００の分子量で１，２型の二重結合
が５０％以上のブタジェン重合体をエポキシ化してエポ
キシ基の含育量がブタジェン重合体１００ｇに対して０
．３モル以上であるエポキシ化ブタジェン重合体１００
重量部
（Ｂ）テトラブロモビスフェノールＡ
２０〜１００重量部
（Ｃ）一般式
（式中Ｒ１およびＲ２は水素又はメチル基を表わし、ｎ
は０から５の整数を表わす）
で示される（メタ）アクリル化合物２０〜１００重量部
を必須成分とする電気特性、耐熱性の優れた難燃化され
た積層板用樹脂組成物である。That is, the present invention is directed to (A) epoxidizing a butadiene polymer with a molecular weight of 500 to 5000 and 50% or more of 1,2 type double bonds so that the content of epoxy groups is 0 per 100 g of the butadiene polymer.
．． Epoxidized butadiene polymer 100 which is 3 moles or more
Part by weight (B) Tetrabromobisphenol A 20 to 100 parts by weight (C) General formula (wherein R1 and R2 represent hydrogen or a methyl group, n
represents an integer from 0 to 5) This is a flame-retardant resin composition for laminates, which contains 20 to 100 parts by weight of a (meth)acrylic compound represented by the following as an essential component and has excellent electrical properties and heat resistance.
本発明の（Ａ）成分の出発原料である５００〜５０００
の分子量で１，２型の二重結合が５０％以上のブタジェ
ン重合体は従来公知の方法で製造される。500 to 5000, which is the starting material for component (A) of the present invention.
A butadiene polymer having a molecular weight of 50% or more of 1,2 type double bonds can be produced by a conventionally known method.
すなわち、炭化水素溶媒中でリチウム、ナトリウムなど
のアルカリ金属またはそれらの有機金属化合物を触媒と
してブタジェンを単独重合させたもの、ある“いはブタ
ジェンとスチレン等のとニルモノマーとを共重合させた
もの、ブタジェンとイソプレン等のジオレフィンとを共
重合させたものなどのブタジェンと他のビニル七ツマ−
を５０モル％以下共重合させるブタジェン共重合体が好
ましく用いられる。また、ナフタレン、アントラセンの
如き多環芳香族化合物を活性化剤としてテトラヒドロフ
ランのような極性溶媒中でナトリウムのようなアルカリ
金属を触媒としてブタジェンを単独または共重合させた
ものも好ましく用いられる。またこれらの重合体末端に
水酸基、カルボキシル基、エポキシ基を導入したいわゆ
るテレケリツクポリマーも同様に用いられる。That is, butadiene is homopolymerized in a hydrocarbon solvent using an alkali metal such as lithium or sodium or an organometallic compound thereof as a catalyst, or a copolymerization of butadiene and a monomer such as styrene is used. Copolymerization of butadiene and diolefins such as isoprene, etc.
A butadiene copolymer having 50 mol% or less of copolymerized is preferably used. Also preferably used are butadiene monopolymerized or copolymerized with an alkali metal such as sodium as a catalyst in a polar solvent such as tetrahydrofuran using a polycyclic aromatic compound such as naphthalene or anthracene as an activator. In addition, so-called telechelic polymers in which hydroxyl groups, carboxyl groups, and epoxy groups are introduced at the terminals of these polymers can also be used.
ブタジェン重合体のエポキシ化は従来公知のエポキシ化
方法で製造される。すなわち、ブタジェン重合体に常温
〜１００℃の温度で過酸化物例えば過酢酸を作用させる
かあるいは過酸化水素と酢酸、または蟻酸を反応系中で
作用させて過酢酸あるいは過蟻酸を発生させ、これら過
酸とブタジェン重合体を反応させることにより合成する
ことができる。このエポキシ化ブタジェン重合体中のエ
ポキシ基の含を量は、ブタジェン重合体１００ｇに対し
０．３モル以上、好ましくは０．４〜０゜７モルである
ことが、優れた積層板を得るのに必要である。The butadiene polymer is epoxidized using a conventionally known epoxidation method. That is, peroxide such as peracetic acid is reacted on a butadiene polymer at a temperature of room temperature to 100°C, or hydrogen peroxide and acetic acid or formic acid are reacted in a reaction system to generate peracetic acid or performic acid. It can be synthesized by reacting a peracid with a butadiene polymer. In order to obtain an excellent laminate, the content of epoxy groups in this epoxidized butadiene polymer should be 0.3 mol or more, preferably 0.4 to 0.7 mol, per 100 g of the butadiene polymer. is necessary.
本発明の（Ｂ）成分であるテトラブロモビスフェノール
Ａは
化学式
で表わされる化合物である
本発明においては（Ｂ）成分の一部をノボラック型フェ
ノール樹脂、臭素化ノボラック型フェノール樹脂あるい
はポリビニルフェノール、臭素化ポリビニルフェノール
で置きかえることも可能である。Tetrabromobisphenol A, which is component (B) of the present invention, is a compound represented by the chemical formula. It is also possible to replace it with polyvinylphenol.
前記のノボラック型フェノール樹脂は従来公知の方法で
製造される。フェノールやクレゾール等のアルキルフェ
ノール類を酸性触媒存在下でホルムアルデヒドと反応さ
せることにより製造されるもので、２以上の複数個の芳
香族核を有するものである。ポリビニルフェノールはビ
ニルフェノール類の重合、例えばｐ−ビニルフェノール
を重合させることによって得られるポリ−ｐ−ビニルフ
ェノール（商品名レジンＭ１丸善石油■）などが代表的
なものである。これらの使用量は通常エポキシ化ブタジ
ェン重合体１００重量部に対し、２０〜１００重量部、
好ましくは３０〜６０重量部用いられる。The above-mentioned novolac type phenolic resin is produced by a conventionally known method. It is produced by reacting alkylphenols such as phenol and cresol with formaldehyde in the presence of an acidic catalyst, and has two or more aromatic nuclei. A representative example of polyvinylphenol is poly-p-vinylphenol (trade name: Resin M1 Maruzen Sekiyu ■) obtained by polymerizing vinylphenols, such as p-vinylphenol. The amount used is usually 20 to 100 parts by weight per 100 parts by weight of the epoxidized butadiene polymer.
Preferably, 30 to 60 parts by weight are used.
本発明の（Ｃ）成分である一般式
（式中Ｒ１およびＲ２は水素又はメチル基を表わし、ｎ
は０から５の整数を表わす）
で示される（メタ）アクリル化合物はテトラブロモビス
フェノールＡに（メタ）アクリル酸クロライドを反応さ
せるか、テトラブロモビスフェノールＡにエチレンオキ
シドあるいはプロピレンオキシドを反応させた後、（メ
タ）アクリル酸を反応させる従来公知の方法で製造され
る。Component (C) of the present invention has the general formula (wherein R1 and R2 represent hydrogen or a methyl group, n
(represents an integer from 0 to 5) The (meth)acrylic compound represented by (represents an integer from 0 to 5) is obtained by reacting tetrabromobisphenol A with (meth)acrylic acid chloride, or by reacting tetrabromobisphenol A with ethylene oxide or propylene oxide. It is produced by a conventionally known method of reacting meth)acrylic acid.
本発明において（Ｃ）成分の一部を（メタ）アクリルモ
ノマー例えばジエチレングリコールジ（メタ）アクリレ
ート、トリメチロールプロパントリ（メタ）アクリレー
トなどで置きかえることも可能である。In the present invention, it is also possible to replace a part of component (C) with a (meth)acrylic monomer such as diethylene glycol di(meth)acrylate, trimethylolpropane tri(meth)acrylate, or the like.
これらの使用量はエポキシ化ポリブタジェン重合体１０
０重量部に対して、２０〜１００ｔｉ量部、好ましくは
３０〜６０重量部である。The amount used is 10% of the epoxidized polybutadiene polymer.
The amount is from 20 to 100 parts by weight, preferably from 30 to 60 parts by weight.
本発明においては（Ｂ）成分は（Ａ）成分中のエポキシ
基と反応し、（Ｃ）成分は（Ａ）成分中の１．２結合型
の二重結合と反応する。したがって架橋密度が高く、強
度の優れた、ガラス転移温度の高い硬化物が得られる。In the present invention, component (B) reacts with the epoxy group in component (A), and component (C) reacts with the 1.2 bond type double bond in component (A). Therefore, a cured product with a high crosslinking density, excellent strength, and a high glass transition temperature can be obtained.
したがって本発明では反応を促進するため必要に応じて
触媒を添加することもできる。Therefore, in the present invention, a catalyst may be added as necessary to promote the reaction.
触媒としては、Ｎ、Ｎ−ジメチルベンジルアミンのよう
な第三アミン、２−エチル−４−メチルイミダゾール等
のイミダゾール類が好ましく用いられる。また、ＢＦｉ
や有機酸とアミンとの錯体も潜在型として用いられる。As the catalyst, tertiary amines such as N,N-dimethylbenzylamine and imidazoles such as 2-ethyl-4-methylimidazole are preferably used. Also, BFi
Complexes of organic acids and amines are also used as latent forms.
さらに有材パーオキシドなどを添加すると（Ａ）成分と
（Ｃ）成分の反応が促進され有利である。Furthermore, it is advantageous to add a material peroxide or the like to promote the reaction between component (A) and component (C).
本発明の樹脂組成物を用いて積層板を製造するには、ま
ず本発明の樹脂組成物を適当な有機溶媒、例えばアセト
ン、メチルエチルケトンなどに溶解してフェスとし、基
材を含浸させた後、乾燥させて積層板用プリプレグを作
る。基材としてはガラス不織布、ガラスクロス、合成繊
維不織布、合成繊維布、紙、綿布などが用いられる。こ
のようにして得られたプリプレグは粘着性がなく取扱い
易いものである。To produce a laminate using the resin composition of the present invention, first, the resin composition of the present invention is dissolved in a suitable organic solvent such as acetone or methyl ethyl ketone to form a fest, and the base material is impregnated with the fest. Dry to make prepreg for laminates. As the base material, glass nonwoven fabric, glass cloth, synthetic fiber nonwoven fabric, synthetic fiber cloth, paper, cotton cloth, etc. are used. The prepreg thus obtained is non-tacky and easy to handle.
これを積層板に成形加工するには通常の熱圧ブレスがそ
のまま用いられる。すなわち、成形温度１５０〜２００
℃、成形圧力２０〜１００ｋｇ／ｃｊ、成形時間３０〜
１２０分が適当な条件として採用される。成形の際には
該プリプレグを重ね、その上に銅箔を重ねて成形し良好
な銅張積層板が得られる。To form this into a laminate, a normal hot press press can be used as is. That is, the molding temperature is 150 to 200
℃, molding pressure 20~100kg/cj, molding time 30~
120 minutes is adopted as a suitable condition. During molding, the prepreg is layered, and a copper foil is layered on top of the prepreg to form a good copper-clad laminate.
このようにして作られた積層板は電気特性とりわけ誘電
特性に優れ、ガラス転移温度が高く、がつ吸湿性、耐化
学薬品性、耐熱性にも優れたものであった。The laminate thus produced had excellent electrical properties, especially dielectric properties, a high glass transition temperature, and excellent moisture absorption, chemical resistance, and heat resistance.
以下に具体的な例を挙げて本発明をさらに詳細に説明す
る。The present invention will be explained in more detail by giving specific examples below.
実施例１
１．２結合が６２％で数平均分子量が１５００の日石ポ
リブタジェンをエポキシ化してエポキシ基の含有量がブ
タジェン重合体１００ｇに対して０．５モルのエポキシ
化ブタジェン重合体を得た。Example 1 Nisseki polybutadiene with a 1.2 bond of 62% and a number average molecular weight of 1500 was epoxidized to obtain an epoxidized butadiene polymer with an epoxy group content of 0.5 mol per 100 g of butadiene polymer. .
このエポキシ化ブタジェン重合体１００重量部、（Ｂ）
成分であるテトラブロモビスフェノールＡ４０！ｌｕ部
、（Ｃ）成分であるピロガードＧＸ−６０９４（第一工
業製薬株式会社の商品名）６０重量部と２−エチル−４
−メチルイミダゾール０゜０５重量部をメチルエチルケ
トン１６０１ｉ量部に溶解し含浸ワニスを得た。100 parts by weight of this epoxidized butadiene polymer, (B)
Ingredient Tetrabromobisphenol A40! lu part, 60 parts by weight of Pyrogard GX-6094 (trade name of Daiichi Kogyo Seiyaku Co., Ltd.), which is the component (C), and 2-ethyl-4
-0.05 parts by weight of methylimidazole was dissolved in 1601 parts by weight of methyl ethyl ketone to obtain an impregnated varnish.
このワニスにガラス布基材（商品名Ｈ−７６２８−３Ｅ
旭ファイバーグラス社製）を含浸し１３０℃で２０分
乾燥してプリプレグを得た。This varnish was coated with a glass cloth base material (product name H-7628-3E).
(manufactured by Asahi Fiberglass Co., Ltd.) was impregnated and dried at 130°C for 20 minutes to obtain a prepreg.
このプリプレグを８枚重ね、その両面に電解銅箔（Ｊ
ＴＣ泊３５μｍ１日鉱グールドフォイル社製）をひき、
温度１８０℃、圧力３０ｋｇ／ｃ−で１２０分、温度２
００℃、圧力３０贈／Ｃ−で１２０分間プレス成形を行
ない両面銅張積層板を得た。Eight sheets of this prepreg are stacked, and electrolytic copper foil (J
Grind TC Tomari 35 μm (manufactured by Nikko Gould Foil Co.),
Temperature 180℃, pressure 30kg/c- for 120 minutes, temperature 2
Press molding was carried out at 00° C. and a pressure of 30° C. for 120 minutes to obtain a double-sided copper-clad laminate.
この積層板の性能試験（ＪＩＳ Ｃ６４８１に準拠）
の結果を表１に示した。Performance test of this laminate (based on JIS C6481)
The results are shown in Table 1.
比較例１
エポキシ樹脂としてテトラブロモビスフェノールＡを骨
格とした難燃性エポキシ樹脂（商品名アラルダイト８０
１１、チバガイギー社製）１００重量部、ジシアンジア
ミド４重量部、ジメチルベンジルアミン０．２重量部を
ジメチルホルムアミド１４１！Ｅ１部、メチルエチルケ
トン８０重量部に溶解しワニスを得た。このワニスに実
施例１で使用したガラス布基材を含浸し、１３０℃で１
５分乾燥してプリプレグを得た。Comparative Example 1 A flame-retardant epoxy resin with tetrabromobisphenol A as the skeleton (trade name: Araldite 80
11, manufactured by Ciba Geigy), 100 parts by weight of dicyandiamide, 0.2 parts by weight of dimethylbenzylamine, and 141 parts by weight of dimethylformamide! A varnish was obtained by dissolving 1 part of E and 80 parts by weight of methyl ethyl ketone. The glass cloth base material used in Example 1 was impregnated with this varnish and heated to 130°C for 1 hour.
A prepreg was obtained by drying for 5 minutes.
このプリプレグを８枚重ね、その両面に実施例１で用い
た電解鋼箔をひき、温度１８０℃、圧力３０ｋｇ／ｃｊ
で１２０分間プレス成形を行ない両面銅張積層板を得た
。この積層板の性能試験の結果を表１に示した。Eight sheets of this prepreg were stacked, the electrolytic steel foil used in Example 1 was lined on both sides, and the temperature was 180°C and the pressure was 30kg/cj.
Press molding was performed for 120 minutes to obtain a double-sided copper-clad laminate. Table 1 shows the results of the performance test of this laminate.
実施例２
１．２結合が６４％で数平均分子量が１８００の日石ポ
リブタジェンをエポキシ化してエポキシ基の含有量がブ
タジェン重合体１００ｇに対して０．４モルのエポキシ
化ブタジェン重合体を得た。Example 2 Nisseki polybutadiene with a 1.2 bond of 64% and a number average molecular weight of 1800 was epoxidized to obtain an epoxidized butadiene polymer with an epoxy group content of 0.4 mol per 100 g of butadiene polymer. .
このエポキシ化ブタジェン重合体１００．重量部、（Ｂ
）成分であるテトラブロモビスフェノールＡ５０重量部
、（Ｃ）成分であるピロガードＧＸ−６０９４（第一工
業製薬株式会社の商品名）５０重量部、２−エチル−４
−メチルイミダゾール０゜０５重量部とジクミルパーオ
キサイド２重量部をメチルエチルケトン１６０重量部に
溶解し含浸ワニスを得た。This epoxidized butadiene polymer 100. Parts by weight, (B
) component tetrabromobisphenol A 50 parts by weight, component (C) pyroguard GX-6094 (trade name of Daiichi Kogyo Seiyaku Co., Ltd.) 50 parts by weight, 2-ethyl-4
-0.05 parts by weight of methylimidazole and 2 parts by weight of dicumyl peroxide were dissolved in 160 parts by weight of methyl ethyl ketone to obtain an impregnated varnish.
このワニスにガラス不織布を含浸し１３０℃で２０分乾
燥し、タックのないプリプレグを得た。A glass nonwoven fabric was impregnated with this varnish and dried at 130°C for 20 minutes to obtain a tack-free prepreg.
このプリプレグを６枚重ね、その両面に電解銅箔（Ｊ
ＴＣ泊３５μｍ１日鉱グールドフォイル社製）をひき、
温度１８０℃、圧力３０ｋｇ／ｃ−で１８０分間成形を
行ない両面鋼張積層板を得た。この積層板の性能試験の
結果を表１に示した。Six sheets of this prepreg are stacked, and electrolytic copper foil (J
Grind TC Tomari 35 μm (manufactured by Nikko Gould Foil Co.),
Molding was performed for 180 minutes at a temperature of 180° C. and a pressure of 30 kg/c to obtain a double-sided steel clad laminate. Table 1 shows the results of the performance test of this laminate.
比較例２
１．２−結合が６４％で数平均分子量が１８００の日石
ポリブタジェンをエポキシ化してエポキシ基の含有量が
ブタジェン重合体１００ｇに対して０６４モルのエポキ
シ化ブタジェン重合体を得た。このエポキシ化ブタジェ
ン重合体１００重量部とノボラック型フェノール樹脂（
商品名ＢＲＭ−５５８、昭和ユニオン合成社製）２４重
量部、テトラブロモビスフェノールＡ４６重量部と２−
エチル−４−メチルイミダゾール１．５重量部をメチル
エチルケトン１０２重量部に溶解し含浸ワニスを得た。Comparative Example 2 Nisseki polybutadiene having a 1.2-bond of 64% and a number average molecular weight of 1800 was epoxidized to obtain an epoxidized butadiene polymer having an epoxy group content of 064 mol per 100 g of the butadiene polymer. 100 parts by weight of this epoxidized butadiene polymer and novolac type phenol resin (
(trade name BRM-558, manufactured by Showa Union Gosei Co., Ltd.) 24 parts by weight, 46 parts by weight of tetrabromobisphenol A and 2-
An impregnated varnish was obtained by dissolving 1.5 parts by weight of ethyl-4-methylimidazole in 102 parts by weight of methyl ethyl ketone.
このワニスに不織布を含浸し、１５０℃で６分乾燥して
粘着性のないプリプレグを得た。このプリプレグを６枚
重ね、その両面に電解銅箔（ＪＴＣ箔３５μｍ１日鉱グ
ールドフォイル社製）を重ね温度１８０℃、圧力３０
ｋｇ ／ ｃ−で１８０分間成形を行ない両面銅張板を
得た。この積層板の性能試験の結果を表１に示した。A nonwoven fabric was impregnated with this varnish and dried at 150° C. for 6 minutes to obtain a non-stick prepreg. Six sheets of this prepreg were stacked, and electrolytic copper foil (JTC foil 35 μm, manufactured by Ichiko Gould Foil Co., Ltd.) was stacked on both sides at a temperature of 180°C and a pressure of 30°C.
kg/c- for 180 minutes to obtain a double-sided copper clad board. Table 1 shows the results of the performance test of this laminate.
表１の実施例１および実施例２と比較例１および比較例
２の比較からも明らかなように一般のエポキシ積層板に
比べ、本発明の組成物は誘電率、誘電正接などの電気特
性に優れ、しかも耐水性、耐熱性、難燃性などの優れた
積層板であった。As is clear from the comparison of Examples 1 and 2 and Comparative Examples 1 and 2 in Table 1, the composition of the present invention has better electrical properties such as dielectric constant and dielectric loss tangent than general epoxy laminates. It was a laminate with excellent water resistance, heat resistance, and flame retardancy.
特許出願人 日本石油株式会社 手続補正書 昭和６２年４月３日 特許庁長官 殿 唖。Patent applicant: Nippon Oil Co., Ltd. Procedural amendment April 3, 1986 Dear Commissioner of the Patent Office.
、：：
１、事件の表示 特願昭６２−３１１７７号２
、発明の名称 積層板用樹脂組成物３、補正を
する者
事件との関係 特許出願人
名 称 （４４４）日本石油株式会社４、代理人
６、補正により増加する発明の数 変化なし７、補正
の対象 明細書（発明の詳細な説明）８、補正
の内容
〔１〕明細書中、第３頁第３行の「はんだ、耐熱性」と
あるを「はんだ耐熱性」と補正する。, :: 1. Indication of the incident Patent Application No. 1983-31177 2
, Title of invention: Resin composition for laminates 3, Relationship with the case of the person making the amendment Name of patent applicant (444) Nippon Oil Co., Ltd. 4, Agent 6, Number of inventions increased by amendment No change 7, Amendment Target Specification (Detailed Description of the Invention) 8, Contents of Amendment [1] In the specification, the phrase "solder, heat resistance" in the third line of page 3 is amended to read "solder heat resistance."
〔２〕同、第１０頁第６行の「有材パーオキシド」とあ
るを「有機パーオキシド」と補正する。[2] In the same document, page 10, line 6, the phrase "material peroxide" is corrected to "organic peroxide."
〔３〕同、第１２頁第６行及び第１４頁第３行のｒＪＴ
Ｃ泊３５μｍ、Ｊとあるを「ＪＴＣ箔３５μｍｓＪと補
正する。[3] Same, rJT on page 12, line 6 and page 14, line 3
Correct the text "C: 35 μm, J" to "JTC foil: 35 μm sJ.
Claims (1)
重結合が５０％以上のブタジエン重合体をエポキシ化し
てエポキシ基の含有量がブタジエン重合体１００ｇに対
して０．３モル以上であるエポキシ化ブタジエン重合体
１００重量部 （Ｂ）テトラブロモビスフェノールＡ ２０〜１００重量部 （Ｃ）一般式 ▲数式、化学式、表等があります▼ （式中Ｒ＿１およびＲ＿２は水素又はメチル基を表わし
、ｎは０から５の整数を表わす） で示される（メタ）アクリル化合物２０〜１００重量部
を必須成分とする電気特性、耐熱性の優れた難燃化され
た積層板用樹脂組成物。[Scope of Claims] [1] (A) A butadiene polymer with a molecular weight of 500 to 5000 and 50% or more of type 1 and 2 double bonds is epoxidized so that the content of epoxy groups per 100 g of the butadiene polymer is epoxidized. (B) 20 to 100 parts by weight of tetrabromobisphenol A (C) General formula ▲ There are numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 and R_2 are hydrogen or methyl group, and n is an integer from 0 to 5. Resin composition for use.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3117787A JPS63199219A (en) | 1987-02-13 | 1987-02-13 | Resin composition for laminated board |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3117787A JPS63199219A (en) | 1987-02-13 | 1987-02-13 | Resin composition for laminated board |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63199219A true JPS63199219A (en) | 1988-08-17 |
Family
ID=12324163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3117787A Pending JPS63199219A (en) | 1987-02-13 | 1987-02-13 | Resin composition for laminated board |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63199219A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10510680B2 (en) | 2017-09-13 | 2019-12-17 | Kabushiki Kaisha Toshiba | Semiconductor device having electromagnetic wave attenuation layer |
-
1987
- 1987-02-13 JP JP3117787A patent/JPS63199219A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10510680B2 (en) | 2017-09-13 | 2019-12-17 | Kabushiki Kaisha Toshiba | Semiconductor device having electromagnetic wave attenuation layer |
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