JPH03110145A - Production of laminated sheet - Google Patents
Production of laminated sheetInfo
- Publication number
- JPH03110145A JPH03110145A JP24791889A JP24791889A JPH03110145A JP H03110145 A JPH03110145 A JP H03110145A JP 24791889 A JP24791889 A JP 24791889A JP 24791889 A JP24791889 A JP 24791889A JP H03110145 A JPH03110145 A JP H03110145A
- Authority
- JP
- Japan
- Prior art keywords
- epoxy resin
- bisphenol
- tetrapromobisphenol
- obtd
- type 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003822 epoxy resin Substances 0.000 claims abstract description 48
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 48
- 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 claims abstract description 32
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 238000001035 drying Methods 0.000 claims abstract description 5
- 239000000463 material Substances 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 4
- 239000002966 varnish Substances 0.000 claims abstract 4
- 238000000465 moulding Methods 0.000 claims abstract 3
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 238000010030 laminating Methods 0.000 claims description 2
- 230000006866 deterioration Effects 0.000 abstract description 6
- 239000002075 main ingredient Substances 0.000 abstract description 5
- 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 abstract 2
- 239000004593 Epoxy Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000032798 delamination Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910000679 solder Inorganic materials 0.000 description 2
- 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 group 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 1
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 1
- TYOXIFXYEIILLY-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole Chemical compound N1C(C)=CN=C1C1=CC=CC=C1 TYOXIFXYEIILLY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 108010008488 Glycylglycine Proteins 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- YMAWOPBAYDPSLA-UHFFFAOYSA-N glycylglycine Chemical compound [NH3+]CC(=O)NCC([O-])=O YMAWOPBAYDPSLA-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
Landscapes
- Laminated Bodies (AREA)
- Epoxy Resins (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は難燃性で耐熱性に優れ、熱劣化の小さいエポキ
シ樹脂系の積層板の製造方法に関するものである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for manufacturing an epoxy resin-based laminate that is flame retardant, has excellent heat resistance, and has little thermal deterioration.
（従来の技術〕
エポキシ樹脂を含浸乾燥して得たプリプレグを任意枚数
積層し、加熱加圧成形してなるエポキシ樹脂銅張積層板
は、主に産業用エレクトロニクス機器や０Ａｌｌ器等の
プリント配線板用材料として用いられ、その需要が拡大
している。近年、電気・電子分野における小型化、精密
化に伴い、高温使用時での信鯨性を高めるために積層板
の耐熱性の向上が強（求められてきた。(Prior art) Epoxy resin copper-clad laminates, which are made by laminating any number of prepregs obtained by impregnating and drying epoxy resin and forming them under heat and pressure, are mainly used for printed wiring boards such as industrial electronic equipment and 0All devices. In recent years, with the miniaturization and precision in the electrical and electronic fields, there has been a strong demand for improved heat resistance of laminates to improve reliability during high-temperature use. (It has been requested.
耐熱性の向上という目的にはフェノールノボラックエポ
キシ樹脂などの多官能性エポキシ樹脂が使用されるが、
耐熱性の点ではすぐれているけれども硬くて脆いという
問題がある。この対策のひとつとして、三官能性エポキ
シ樹脂をビスフェノールＡ型エポキシ樹脂及びビスフェ
ノールＡあるいはテトラプロモビスフェノールＡと触媒
の存在下で反応して得られるエポキシ樹脂が使われてい
る。しかしながら、この樹脂は粘度が高いので、基材の
含浸性が劣るという欠点があることから、その樹脂にテ
トラプロモビスフェノールＡ型エポキシ樹脂を添加して
低粘度化する方法が行われている（例えば、三井石油化
学製、Ｖ Ｆ−２８０１）が、大きい上に高温ではテト
ラプロモビスフェノールＡ型エポキシ樹脂の臭素原子が
脱離して変色するという欠点があった。Polyfunctional epoxy resins such as phenol novolac epoxy resins are used for the purpose of improving heat resistance.
Although it has excellent heat resistance, it has the problem of being hard and brittle. As one measure against this problem, epoxy resins obtained by reacting trifunctional epoxy resins with bisphenol A type epoxy resins and bisphenol A or tetrapromobisphenol A in the presence of a catalyst are used. However, since this resin has a high viscosity, it has the disadvantage of poor impregnating properties of the base material, so a method of lowering the viscosity by adding tetrapromobisphenol A type epoxy resin to the resin has been carried out (for example , manufactured by Mitsui Petrochemical Co., Ltd., V F-2801), has the disadvantage that it is large and that the bromine atom of the tetrapromobisphenol A type epoxy resin is detached and discolored at high temperatures.
従って、本発明の目的とするところは、耐熱性に優れ、
熱劣化の小さいエポキシ樹脂銅張積層板を提供すること
にある。Therefore, the object of the present invention is to have excellent heat resistance,
An object of the present invention is to provide an epoxy resin copper-clad laminate with little thermal deterioration.
上記目的を達成するために、本発明は、ビスフェノール
Ａ型エポキシ樹脂、三官能エポキシ樹脂、テトラプロモ
ビスフェノールＡ型エポキシ樹脂及びビスフェノールＡ
あるいはテトラプロモビスフェノールＡを触媒の存在下
で反応させたエポキシ樹脂を主剤とし、この主剤と硬化
剤、硬化促進剤及び溶剤から成るフェスを得、これを基
材に含浸乾燥して得たプリプレグを所定数積層成形する
ものである。In order to achieve the above object, the present invention provides a bisphenol A type epoxy resin, a trifunctional epoxy resin, a tetrapromobisphenol A type epoxy resin, and a bisphenol A type epoxy resin.
Alternatively, a prepreg prepared by using an epoxy resin made by reacting tetrapromobisphenol A in the presence of a catalyst as a main ingredient, obtaining a fest consisting of this main ingredient, a curing agent, a curing accelerator, and a solvent, and impregnating and drying this into a base material. A predetermined number of layers are laminated and molded.
上記のフェスの主剤であるエポキシ樹脂を合成するため
の一成分であるテトラプロモビスフェノールＡ型エポキ
シ樹脂は、難燃性に優れており、中でもテトラプロモビ
スフェノールＡジグリシンを起こし易く熱劣化が大きい
、従ってテトラプロモビスフェノールＡジグリシジルエ
ーテルを三官能性エポキシ樹脂、ビスフェノールＡ型エ
ポキシ樹脂及びビスフェノールＡあるいはテトラプロモ
ビスフェノールＡと共に反応させることにより、テトラ
プロモビスフェノールＡジグリシジルエーテルが単体で
残留することはほとんどない。従って、本発明では従来
の技術において、フリーの状態であったテトラプロモビ
スフェノールＡジグリシジルエーテルをビスフェノール
Ａ型エポキシ樹脂などと反応させることにより、耐熱性
に優れ、熱劣化の小さいエポキシ樹脂銅張積層板を得る
ことができる。Tetrapromobisphenol A type epoxy resin, which is one of the components for synthesizing the epoxy resin that is the main ingredient of the above-mentioned FES, has excellent flame retardancy, and is particularly prone to forming tetrapromobisphenol A diglycine, which causes large thermal deterioration. By reacting tetrapromobisphenol A diglycidyl ether with a trifunctional epoxy resin, bisphenol A type epoxy resin, and bisphenol A or tetrapromobisphenol A, tetrapromobisphenol A diglycidyl ether hardly remains alone. Therefore, in the present invention, by reacting tetrapromobisphenol A diglycidyl ether, which was in a free state in the conventional technology, with bisphenol A type epoxy resin, etc., the epoxy resin copper clad laminate has excellent heat resistance and little thermal deterioration. You can get a board.
本発明で使用する三官能エポキシ樹脂としてはトリフエ
ノール類のグリシジルエーテル、芳香族、ジアミンのト
リグリシジルエーテルなどが挙げられる。エポキシ樹脂
のハロゲン含率は難燃性の要求度、積層板用基材の種類
等により種々調整されているが、本発明ではテトラプロ
モビスフェノールＡとテトラプロモビスフェノールＡ型
エポキシ樹脂の二つの配合量によってハロゲン含率をか
えることができ、難燃性を調整することができる。Examples of the trifunctional epoxy resin used in the present invention include glycidyl ethers of triphenols, triglycidyl ethers of aromatics, and diamines. The halogen content of the epoxy resin is variously adjusted depending on the degree of flame retardancy required, the type of substrate for the laminate, etc., but in the present invention, two compounding amounts of tetrapromobisphenol A and tetrapromobisphenol A type epoxy resin are used. By changing the halogen content, flame retardancy can be adjusted.
各成分の好ましい配合割合は、三官能性エポキシ樹ＪＩ
ＩＩＯ〜６０重量部に対し、ビスフェノールＡ型エポキ
シ樹脂５〜３０重量部、テトラプロモビスフェノールＡ
型エポキシ樹脂５〜３０重量部、ビスフェノールＡ又は
テトラプロモビスフェノールＡ１０〜４０重量
である。The preferred blending ratio of each component is trifunctional epoxy resin JI
IIO to 60 parts by weight, bisphenol A type epoxy resin 5 to 30 parts by weight, tetrapromobisphenol A
5 to 30 parts by weight of type epoxy resin, 10 to 40 parts by weight of bisphenol A or tetrapromobisphenol A
It is.
上記割合の範囲からはずれると、過剰の成分が遊離の状
態で残存することになる。三官能性エポキシ樹脂が過剰
の場合、硬化物が硬く、脆くなる傾向にあり、ビスフェ
ノールＡ型エポキシ樹脂及びテトラプロモビスフェノー
ルＡ型エポキシｍ脂が過剰の場合、テトラプロモビスフ
ェノールＡ型エポキシ樹脂が残存しやすく、前述の如き
欠点が生じる。また、ビスフェノールＡ又はテトラビス
フェノールＡが過剰の場合、電気特性、耐熱性などの特
性が低下する。If the ratio is outside the above range, excess components will remain in a free state. If the trifunctional epoxy resin is in excess, the cured product tends to be hard and brittle, and if the bisphenol A epoxy resin and tetrapromobisphenol A epoxy resin are in excess, the tetrapromobisphenol A epoxy resin remains. This is easy and causes the drawbacks mentioned above. Moreover, when bisphenol A or tetrabisphenol A is excessive, properties such as electrical properties and heat resistance are deteriorated.
反応の触媒としては、第三級アミン、四級アンモニウム
塩やイミダゾール類などがある１反応に関しては反応時
間１〜３時間、反応温度を１２０〜２００℃が適当であ
る。好ましくは反応時間１゜５〜２時間、反応温度１５
０〜１８０°Ｃがよい。As for the reaction catalyst, a tertiary amine, a quaternary ammonium salt, an imidazole, etc. are used.For one reaction, a reaction time of 1 to 3 hours and a reaction temperature of 120 to 200°C are appropriate. Preferably, the reaction time is 1°5 to 2 hours, and the reaction temperature is 15°.
The temperature is preferably 0 to 180°C.
実施例
トリフエノール系の三官能性エポキシ樹脂（三井石油化
学製ＶＧ・３１０１、エポキシ当量２１０） ４０重量
部（以下単に「部」という）、ビスフェノールＡ型エポ
キシ樹脂（油化シェル製ＥＰ−８２８、エポキシ当量１
Ｂ？） ２３部、テトラプロモビスフェノールＡ型エポ
キシ樹脂（住友化学製Ｅｓｍ−４００、エポキシ当量４
００） １４部、テトラプロモビスフェノールＡ２０部
、ビスフェノールＡ３部、２部４Ｍ１．０５部を反応温
度１６０℃、反応時間２時間で反応させてエポキシ当量
３９０ブロム化率１８％のエポキシ樹脂を得た。Examples Triphenol-based trifunctional epoxy resin (Mitsui Petrochemical Co., Ltd. VG-3101, epoxy equivalent: 210) 40 parts by weight (hereinafter simply referred to as "parts"), bisphenol A type epoxy resin (Yuka Shell EP-828, Epoxy equivalent 1
B? ) 23 parts, tetrapromobisphenol A type epoxy resin (Esm-400 manufactured by Sumitomo Chemical, epoxy equivalent: 4
00), 20 parts of tetrapromobisphenol A, 3 parts of bisphenol A, and 1.05 parts of 2 parts 4M were reacted at a reaction temperature of 160° C. for a reaction time of 2 hours to obtain an epoxy resin having an epoxy equivalent of 390 and a bromination rate of 18%.
その樹脂１００部とジシアンジアミド２．７部、２−フ
ェニル−４−メチルイミダゾール０．３部をメチルセル
ソルブ溶媒中に溶かしフェスを作り、これをガラス基材
に含浸し乾燥して樹脂量４５％のプリプレグを得た。100 parts of the resin, 2.7 parts of dicyandiamide, and 0.3 parts of 2-phenyl-4-methylimidazole were dissolved in methylcellosolve solvent to make a face, which was impregnated into a glass substrate and dried to give a resin content of 45%. prepreg was obtained.
該プリプレグを２枚積層し、加熱加圧して０．４閣厚の
積層板を得た。その特性を表１に示す。Two sheets of the prepreg were laminated and heated and pressed to obtain a 0.4 mm thick laminate. Its characteristics are shown in Table 1.
比較例
エポキシ樹脂（三井石油化学製Ｖ Ｆ−２８０１、エポ
キシ当量３９０、ブロム化率１８％）１００部とジシア
ンジアミド２．７部、２部４Ｍ２０．３部をメチルセル
ソルブ溶媒中に溶かしフェスを作り、これをガラス基材
に含浸し乾燥して樹脂量４５％のプリプレグを得た。該
プリプレグを２枚積層し、加熱加圧してＱ、 ４ ｒｍ
厚の積層板を得た。その特性を表１に示す。Comparative Example 100 parts of epoxy resin (Mitsui Petrochemical V F-2801, epoxy equivalent: 390, bromination rate: 18%), 2.7 parts of dicyandiamide, 20.3 parts of 2 parts 4M were dissolved in methylcellosolve solvent to make a face. This was impregnated into a glass substrate and dried to obtain a prepreg with a resin content of 45%. Two sheets of the prepreg were laminated and heated and pressurized to a pressure of Q, 4 rm.
A thick laminate was obtained. Its characteristics are shown in Table 1.
表
試験方法
（１）半田耐熱性
プレッシャークツカー１２１℃２時間後、積層板を２８
０℃の半田浴に１８０秒間浮かべ、層間剥離及びミーズ
リングの発生の有無を調べる。Table Test Method (1) Solder Heat Resistance Pressure Heater: After 2 hours at 121°C, the laminate was heated to 28°C.
Float in a solder bath at 0°C for 180 seconds and check for delamination and measling.
Ｏ：層間剥離・ミーズリング無し
×：層間剥離あるいはミーズリング有り〔発明の効果〕
本発明の製造方法に従うことによって、耐熱性に優れ、
熱劣化の小さいエボキキシ樹脂銅張積層板を得ることが
でき、その工業的価値は非常に大きなものである。O: No delamination or measling ×: Delamination or measling [Effects of the invention] By following the manufacturing method of the present invention, it has excellent heat resistance,
It is possible to obtain an epoxy resin copper-clad laminate with little thermal deterioration, and its industrial value is extremely large.
Claims (1)
キシ樹脂、テトラプロモビスフェノールＡ型エポキシ樹
脂及びビスフェノールＡあるいはテトラプロモビスフェ
ノールＡを触媒の存在下で反応させたエポキシ樹脂を主
剤とし、この主剤と硬化剤、硬化促進剤及び溶剤から成
るワニスを基材に含浸乾燥して得たプリプレグを所定数
積層成形することを特徴とするエポキシ樹脂銅張積層板
の製造方法。(1) The main resin is an epoxy resin in which bisphenol A type epoxy resin, trifunctional epoxy resin, tetrapromobisphenol A type epoxy resin, and bisphenol A or tetrapromobisphenol A are reacted in the presence of a catalyst, and this main resin and a curing agent are used. A method for producing an epoxy resin copper-clad laminate, comprising laminating and molding a predetermined number of prepregs obtained by impregnating and drying a base material with a varnish consisting of a curing accelerator and a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24791889A JPH03110145A (en) | 1989-09-26 | 1989-09-26 | Production of laminated sheet |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24791889A JPH03110145A (en) | 1989-09-26 | 1989-09-26 | Production of laminated sheet |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH03110145A true JPH03110145A (en) | 1991-05-10 |
Family
ID=17170493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24791889A Pending JPH03110145A (en) | 1989-09-26 | 1989-09-26 | Production of laminated sheet |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH03110145A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05286075A (en) * | 1992-04-10 | 1993-11-02 | Toshiba Chem Corp | Manufacture of copper-clad laminate |
| JPH05309789A (en) * | 1992-05-13 | 1993-11-22 | Toshiba Chem Corp | Production of composite copper clad laminated sheet |
-
1989
- 1989-09-26 JP JP24791889A patent/JPH03110145A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05286075A (en) * | 1992-04-10 | 1993-11-02 | Toshiba Chem Corp | Manufacture of copper-clad laminate |
| JPH05309789A (en) * | 1992-05-13 | 1993-11-22 | Toshiba Chem Corp | Production of composite copper clad laminated sheet |
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