JPH05140263A - Production of flame-retardant epoxy resin - Google Patents
Production of flame-retardant epoxy resinInfo
- Publication number
- JPH05140263A JPH05140263A JP3309594A JP30959491A JPH05140263A JP H05140263 A JPH05140263 A JP H05140263A JP 3309594 A JP3309594 A JP 3309594A JP 30959491 A JP30959491 A JP 30959491A JP H05140263 A JPH05140263 A JP H05140263A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- flame
- resin
- bisphenol
- retardant epoxy
- 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.)
- Withdrawn
Links
- 239000003822 epoxy resin Substances 0.000 title claims description 43
- 229920000647 polyepoxide Polymers 0.000 title claims description 43
- 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 title claims description 16
- 239000003063 flame retardant Substances 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 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 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 230000001588 bifunctional effect Effects 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 abstract description 23
- 229920005989 resin Polymers 0.000 abstract description 10
- 239000011347 resin Substances 0.000 abstract description 10
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 4
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 abstract description 3
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 abstract description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 description 9
- 239000002966 varnish Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 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
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-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
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000930 thermomechanical effect Effects 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
Landscapes
- Epoxy Resins (AREA)
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、プリント配線板として
用いられる積層板の製造に使用されるＦＲ−４グレード
の難燃性エポキシ樹脂の製造方法に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for producing an FR-4 grade flame-retardant epoxy resin used for producing a laminate used as a printed wiring board.
【０００２】[0002]
【従来の技術】積層板の製造に使用されるＦＲ−４グレ
ードのエポキシ樹脂としては、臭素化ビスフェノールＡ
型エポキシ樹脂にフェノールノボラック型エポキシ樹脂
又はクレゾールノボラック型エポキシ樹脂を配合したも
のが使用されている。Brominated bisphenol A is a FR-4 grade epoxy resin used in the production of laminates.
A type epoxy resin mixed with a phenol novolac type epoxy resin or a cresol novolac type epoxy resin is used.
【０００３】[0003]
【発明が解決しようとする課題】しかし最近の表面実装
の増加やプリント配線基板の薄型化等に伴って、耐湿性
や耐熱性の特性が高度に要求されているが、上記のよう
なエポキシ樹脂ではこれらの特性を十分に向上させるこ
とができないという問題があった。本発明は上記の点に
鑑みてなされたものであり、耐湿性や耐熱性に優れた難
燃性エポキシ樹脂の製造方法を提供することを目的とす
るものである。However, due to the recent increase in surface mounting and the thinning of printed wiring boards, moisture resistance and heat resistance are highly required. However, the epoxy resin as described above is required. However, there is a problem that these characteristics cannot be sufficiently improved. The present invention has been made in view of the above points, and an object of the present invention is to provide a method for producing a flame-retardant epoxy resin having excellent moisture resistance and heat resistance.
【０００４】[0004]
【課題を解決するための手段】本発明に係る難燃性エポ
キシ樹脂の製造方法は、構造式が次の式１で示される２
官能エポキシ樹脂と、In the method for producing a flame-retardant epoxy resin according to the present invention, the structural formula 2 is represented by the following formula 1.
Functional epoxy resin,
【０００５】[0005]
【化２】 [Chemical 2]
【０００６】（Ｒは炭素数１〜４のアルキル基、ｍは０
〜１０の整数、ｎは０〜３の整数）テトラブロモビスフ
ェノールＡとを反応させることを特徴とするものであ
る。以下、本発明を詳細に説明する。上記の式１で示さ
れる２官能エポキシ樹脂をテトラブロモビスフェノール
Ａと反応させるにあたって、さらにビスフェノールＡ型
エポキシ樹脂やビスフェノールＡを配合して反応させる
こともできる。ビスフェノールＡ型エポキシ樹脂として
はエポキシ当量が１８０〜１９０ｇ／ｅｑのものが好ま
しく、式１の２官能エポキシ樹脂１当量に対してビスフ
ェノールＡ型エポキシ樹脂を０〜０．８当量の範囲で配
合するのが好ましい。またテトラブロモビスフェノール
Ａは式１で示される２官能エポキシ樹脂とビスフェノー
ルＡ型エポキシ樹脂の合計の当量数に対して１／４〜１
／２の当量数の範囲で配合するのが好ましい。さらにビ
スフェノールＡは式１で示される２官能エポキシ樹脂と
ビスフェノールＡ型エポキシ樹脂の合計の当量数に対し
て１／５以下当量数で配合するのが好ましい。(R is an alkyl group having 1 to 4 carbon atoms, m is 0
It is characterized in that tetrabromobisphenol A is reacted with an integer of 10 to 10, and n is an integer of 0 to 3. Hereinafter, the present invention will be described in detail. When the bifunctional epoxy resin represented by the above formula 1 is reacted with tetrabromobisphenol A, a bisphenol A type epoxy resin or bisphenol A can be further mixed and reacted. The bisphenol A type epoxy resin preferably has an epoxy equivalent of 180 to 190 g / eq, and the bisphenol A type epoxy resin is compounded in the range of 0 to 0.8 equivalent to 1 equivalent of the bifunctional epoxy resin of the formula 1. Is preferred. Further, tetrabromobisphenol A is 1/4 to 1 with respect to the total equivalent number of the bifunctional epoxy resin represented by Formula 1 and the bisphenol A type epoxy resin.
It is preferable to blend in the range of the equivalent number of / 2. Further, bisphenol A is preferably blended in an amount of 1/5 or less of the total equivalent number of the bifunctional epoxy resin represented by Formula 1 and the bisphenol A type epoxy resin.
【０００７】上記のように式１で示される２官能エポキ
シ樹脂にテトラブロモビスフェノールＡ、及び必要に応
じてビスフェノールＡ型エポキシ樹脂やビスフェノール
Ａを配合し、これを触媒の存在下で反応させることによ
って、臭素化させた難燃性エポキシ樹脂を調製すること
ができる。触媒としては、テトラメチルアンモニウムク
ロライド、テトラエチルアンモニウムクロライド、２−
エチル−４−メチルイミダゾール、２−メチルイミダゾ
ール、ベンジルアミンなどを用いることができる。また
反応は、１４０〜１８０℃に加熱しながら２〜４時間お
こなわせるようにするのがよい。As described above, tetrabromobisphenol A and, if necessary, bisphenol A type epoxy resin or bisphenol A are mixed with the bifunctional epoxy resin represented by the formula 1 and reacted in the presence of a catalyst. A brominated flame-retardant epoxy resin can be prepared. As the catalyst, tetramethylammonium chloride, tetraethylammonium chloride, 2-
Ethyl-4-methylimidazole, 2-methylimidazole, benzylamine and the like can be used. The reaction is preferably carried out for 2 to 4 hours while heating at 140 to 180 ° C.
【０００８】上記のようにして得られる難燃性エポキシ
樹脂を溶剤に溶解させてワニスを調製し、このワニスを
ガラス布等の基材に含浸させて乾燥することによってプ
リプレグを作成することができる。そしてこのプリプレ
グを複数枚重ねると共に必要に応じて銅箔等の金属箔を
重ねて加熱加圧をおこなって積層成形することによっ
て、プリント配線板に加工されるＦＲ−４グレードのガ
ラス布基材エポキシ樹脂積層板を得ることができる。ま
たこのプリプレグを接着用プリプレグとして用いて内層
回路板と外層材とを積層することによってＦＲ−４グレ
ードのガラス布基材エポキシ樹脂多層積層板を得ること
ができる。A prepreg can be prepared by dissolving the flame-retardant epoxy resin obtained as described above in a solvent to prepare a varnish, impregnating the varnish with a base material such as glass cloth and drying the varnish. . FR-4 grade glass cloth base epoxy processed into printed wiring boards by stacking a plurality of these prepregs and stacking metal foils such as copper foils as necessary to heat and pressurize them for laminate molding. A resin laminated board can be obtained. Further, by using this prepreg as an adhesive prepreg and laminating an inner layer circuit board and an outer layer material, an FR-4 grade glass cloth base material epoxy resin multilayer laminated board can be obtained.
【０００９】[0009]
【実施例】以下本発明を実施例によって例証する。 （実施例１）式１で示される２官能エポキシ樹脂（日本
化薬株式会社製「ＲＥ−７０１」：エポキシ当量１４５
ｇ／ｅｑ）５００ｇにテトラブロモビスフェノールＡ３
００ｇを配合してフラスコに仕込み、Ｎ2 ガスの不活性
雰囲気下でテトラメチルアンモニウムクロライドを触媒
として１５０℃で２時間反応させた。反応終了後２００
ｇのメチルエチルケトンを添加して臭素化した難燃性エ
ポキシ樹脂を得た。この難燃性エポキシ樹脂のエポキシ
当量は３５０ｇ／ｅｑであった。EXAMPLES The present invention will now be illustrated by examples. (Example 1) Bifunctional epoxy resin represented by Formula 1 ("RE-701" manufactured by Nippon Kayaku Co., Ltd .: epoxy equivalent 145)
g / eq) 500 g of tetrabromobisphenol A3
00 g was blended and charged into a flask, and reacted at 150 ° C. for 2 hours using tetramethylammonium chloride as a catalyst in an inert atmosphere of N 2 gas. 200 after the reaction
g of methyl ethyl ketone was added to obtain a brominated flame-retardant epoxy resin. The epoxy equivalent of this flame-retardant epoxy resin was 350 g / eq.
【００１０】（実施例２）式１で示される２官能エポキ
シ樹脂（日本化薬株式会社製「ＲＥ−７０１」：エポキ
シ当量１４５ｇ／ｅｑ）２５０ｇ及びビスフェノールＡ
型エポキシ樹脂（三井石油化学株式会社製「Ｒ−１４
０」：エポキシ当量１８５ｇ／ｅｑ）２５０ｇにテトラ
ブロモビスフェノールＡ３００ｇを配合してフラスコに
仕込み、後は実施例１と同様にして臭素化した難燃性エ
ポキシ樹脂を得た。この難燃性エポキシ樹脂のエポキシ
当量は４２０ｇ／ｅｑであった。(Example 2) 250 g of a bifunctional epoxy resin represented by the formula 1 ("RE-701" manufactured by Nippon Kayaku Co., Ltd .: epoxy equivalent 145 g / eq) and bisphenol A.
Epoxy resin (Mitsui Petrochemical Co., Ltd. "R-14
0 ": 250 g of epoxy equivalent 185 g / eq) and 300 g of tetrabromobisphenol A were blended and charged into a flask. Then, a brominated flame-retardant epoxy resin was obtained in the same manner as in Example 1. The epoxy equivalent of this flame-retardant epoxy resin was 420 g / eq.
【００１１】（比較例）ビスフェノールＡ型エポキシ樹
脂（三井石油化学株式会社製「Ｒ−１４０」：エポキシ
当量１８５ｇ／ｅｑ）５００ｇにテトラブロモビスフェ
ノールＡ３００ｇを配合してフラスコに仕込み、後は実
施例１と同様にして臭素化した難燃性エポキシ樹脂を得
た。この難燃性エポキシ樹脂のエポキシ当量は５２０ｇ
／ｅｑであった。Comparative Example 500 g of bisphenol A type epoxy resin (“R-140” manufactured by Mitsui Petrochemical Co., Ltd .: epoxy equivalent 185 g / eq) was mixed with 300 g of tetrabromobisphenol A and charged into a flask. A brominated flame-retardant epoxy resin was obtained in the same manner as in. The epoxy equivalent of this flame-retardant epoxy resin is 520 g.
It was / eq.
【００１２】上記実施例１，２及び比較例で得た難燃性
エポキシ樹脂に表１に示す量で硬化剤、硬化促進剤及び
溶剤を配合してエポキシ樹脂ワニスを得た。尚、次表に
おいて難燃性エポキシ樹脂は固形分８０％溶液としての
量である。The flame-retardant epoxy resins obtained in Examples 1 and 2 and Comparative Example were mixed with a curing agent, a curing accelerator and a solvent in the amounts shown in Table 1 to obtain epoxy resin varnishes. In the following table, the flame-retardant epoxy resin is the amount as a solution having a solid content of 80%.
【００１３】[0013]
【表１】 [Table 1]
【００１４】上記のように調製したエポキシ樹脂ワニス
を７６２８タイプのガラス布に含浸させて乾燥すること
によって、樹脂含浸量が約５０％、１７０℃でのゲルタ
イムが１５０〜２００秒のプリプレグを作成し、このプ
リプレグをもみほぐして表面のＢステージ状態の樹脂粉
をもみ取り、予め窓をあけたクラフト紙を重ねてこの窓
にＢステージ状態の樹脂粉を入れ、離型フィルムを介し
て金属プレートで挟んでこれを１７０℃、４０ｋｇ／ｃ
ｍ2 で成形プレスすることによって、樹脂硬化物を作成
した。この樹脂硬化物についてガラス転移温度（Ｔｇ）
を熱機械分析（ＴＭＡ）で測定すると共に、６０℃、９
０％ＲＨ、１００時間の条件で吸湿させたときの吸湿率
と、臭素含有率を測定した。結果を表２に示す。A glass cloth of 7628 type is impregnated with the epoxy resin varnish prepared as described above and dried to prepare a prepreg having a resin impregnation amount of about 50% and a gel time at 170 ° C. of 150 to 200 seconds. , Crush the prepreg to scrape off the B-stage resin powder on the surface, stack the kraft paper with a pre-opened window and put the B-stage resin powder in this window, and then use a metal plate through the release film. Sandwich this at 170 ℃, 40kg / c
A resin cured product was prepared by molding and pressing at m 2 . Glass transition temperature (Tg) of this cured resin
Is measured by thermomechanical analysis (TMA),
The moisture absorption rate and the bromine content rate when moisture was absorbed under conditions of 0% RH and 100 hours were measured. The results are shown in Table 2.
【００１５】[0015]
【表２】 [Table 2]
【００１６】表２にみられるように、各実施例のものは
ガラス転移温度が高く耐熱性が優れており、また吸湿率
が低く耐湿性が優れていることが確認される。As shown in Table 2, it is confirmed that each of the examples has a high glass transition temperature and excellent heat resistance, and also has a low moisture absorption rate and excellent moisture resistance.
【００１７】[0017]
【発明の効果】上記のように本発明は、式１で示される
２官能エポキシ樹脂にテトラブロモビスフェノールＡを
反応させるようにしたものであり、テトラブロモビスフ
ェノールＡによる臭素化で難燃性エポキシ樹脂を得るこ
とができると共に、式１で示される２官能エポキシ樹脂
によって耐湿性や耐熱性を高めることができるものであ
る。As described above, according to the present invention, the bifunctional epoxy resin represented by the formula 1 is reacted with tetrabromobisphenol A. The flame retardant epoxy resin is brominated with tetrabromobisphenol A. And the bifunctional epoxy resin represented by the formula 1 can enhance the moisture resistance and the heat resistance.
Claims (1)
キシ樹脂と、 【化１】 （Ｒは炭素数１〜４のアルキル基、ｍは０〜１０の整
数、ｎは０〜３の整数）テトラブロモビスフェノールＡ
とを反応させることを特徴とする難燃性エポキシ樹脂の
製造方法。1. A bifunctional epoxy resin having a structural formula represented by the following formula 1, and: (R is an alkyl group having 1 to 4 carbon atoms, m is an integer of 0 to 10 and n is an integer of 0 to 3) Tetrabromobisphenol A
A method for producing a flame-retardant epoxy resin, which comprises reacting with
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3309594A JPH05140263A (en) | 1991-11-26 | 1991-11-26 | Production of flame-retardant epoxy resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3309594A JPH05140263A (en) | 1991-11-26 | 1991-11-26 | Production of flame-retardant epoxy resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH05140263A true JPH05140263A (en) | 1993-06-08 |
Family
ID=17994915
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3309594A Withdrawn JPH05140263A (en) | 1991-11-26 | 1991-11-26 | Production of flame-retardant epoxy resin |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH05140263A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0661322A3 (en) * | 1993-12-21 | 1995-08-16 | Shell Int Research |
-
1991
- 1991-11-26 JP JP3309594A patent/JPH05140263A/en not_active Withdrawn
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0661322A3 (en) * | 1993-12-21 | 1995-08-16 | Shell Int Research |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A300 | Withdrawal of application because of no request for examination |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 19990204 |