JPH04372644A - Phenol resin composition - Google Patents
Phenol resin compositionInfo
- Publication number
- JPH04372644A JPH04372644A JP15072291A JP15072291A JPH04372644A JP H04372644 A JPH04372644 A JP H04372644A JP 15072291 A JP15072291 A JP 15072291A JP 15072291 A JP15072291 A JP 15072291A JP H04372644 A JPH04372644 A JP H04372644A
- Authority
- JP
- Japan
- Prior art keywords
- phenol
- resin
- phenol resin
- liq
- compsn
- 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
- 239000005011 phenolic resin Substances 0.000 title claims abstract description 17
- 239000000203 mixture Substances 0.000 title claims description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- WHOZNOZYMBRCBL-OUKQBFOZSA-N (2E)-2-Tetradecenal Chemical compound CCCCCCCCCCC\C=C\C=O WHOZNOZYMBRCBL-OUKQBFOZSA-N 0.000 claims abstract description 11
- 229940044654 phenolsulfonic acid Drugs 0.000 claims abstract description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011256 inorganic filler Substances 0.000 claims description 7
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 7
- 229920001568 phenolic resin Polymers 0.000 claims description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 18
- 229920005989 resin Polymers 0.000 abstract description 10
- 239000011347 resin Substances 0.000 abstract description 10
- 239000003054 catalyst Substances 0.000 abstract description 5
- 229910052751 metal Inorganic materials 0.000 abstract description 5
- 239000002184 metal Substances 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 238000013329 compounding Methods 0.000 abstract description 4
- 238000000465 moulding Methods 0.000 abstract description 4
- 239000000945 filler Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000011134 resol-type phenolic resin Substances 0.000 description 4
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920003987 resole Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- 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
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- -1 organic acid salt Chemical class 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【０００１】0001
【産業上の利用分野】この発明は、フェノール樹脂組成
物に関するものである。さらに詳しくは、この発明は、
ＳＭＣ，ＢＭＣ等に有用な、高強度成形品を提供するこ
とができ、速硬化性で、常温ライフの長い液状レゾール
型フェノール樹脂組成物に関するものである。FIELD OF THE INVENTION This invention relates to phenolic resin compositions. More specifically, this invention
The present invention relates to a liquid resol type phenolic resin composition that can provide high-strength molded products useful for SMC, BMC, etc., has fast curing properties, and has a long life at room temperature.
【０００２】0002
【従来の技術】従来よりフェノール樹脂は電気・電子機
器、機械部品、日用品等の各種の分野において広く使用
されており、ガラス繊維等と複合化したフェノールＳＭ
Ｃ，ＢＭＣ用としても使用されてきている。このＳＭＣ
，ＢＭＣには、液状レゾール型フェノール樹脂を増粘剤
、硬化助剤としてＭｇＯ等の金属酸化物とともに使用し
てきている。[Prior Art] Phenol resin has been widely used in various fields such as electrical and electronic equipment, mechanical parts, and daily necessities.
It has also been used for C and BMC. This SMC
, BMC, liquid resol type phenolic resin has been used together with metal oxides such as MgO as a thickener and curing aid.
【０００３】0003
【発明が解決しようとする課題】しかしながら、フェノ
ールＳＭＣ，ＢＭＣに用いる液状レゾール型フェノール
樹脂の従来のものは、樹脂コンパウンドの増粘が早いた
め、樹脂を使用しようとする際の作業性が悪く、また、
ガラス繊維への含浸が不充分になるという欠点があった
。このため、成形品の強度向上にも制約があった。[Problems to be Solved by the Invention] However, conventional liquid resol type phenol resins used for phenol SMC and BMC have poor workability when using the resin because the resin compound thickens quickly. Also,
There was a drawback that impregnation into glass fibers was insufficient. For this reason, there were restrictions on improving the strength of molded products.
【０００４】また、フェノール樹脂に金属酸化物に代え
てスルホン酸等の酸を添加する方法も知られているが、
これらの酸類の使用でも増粘は早く、また、金属部品、
金型の腐食の問題がある。このため、従来のフェノール
樹脂組成物の場合には、速硬化性を有しつつ、しかも常
温でのライフの長い液状レゾール型フェノール樹脂組成
物は実現されていなかった。[0004]Also, a method is known in which an acid such as sulfonic acid is added to a phenol resin instead of a metal oxide.
Even with the use of these acids, the viscosity increases quickly, and metal parts,
There is a problem with mold corrosion. For this reason, in the case of conventional phenol resin compositions, a liquid resol type phenol resin composition that has fast curing properties and has a long life at room temperature has not been realized.
【０００５】この発明は、以上の通りの事情に鑑みてな
されたものであり、従来の液状レゾール型フェノール樹
脂組成物の欠点を解消し、高強度成形品を提供すること
ができ、ＳＭＣ，ＢＭＣ用に適した速硬化性を有し、し
かも常温ライフの長いフェノール樹脂組成物を提供する
ことを目的としている。The present invention has been made in view of the above-mentioned circumstances, and is capable of solving the drawbacks of conventional liquid resol type phenolic resin compositions and providing high-strength molded products. The object of the present invention is to provide a phenolic resin composition that has fast curing properties suitable for various uses and has a long life at room temperature.
【０００６】[0006]
【課題を解決するための手段】この発明は、上記の課題
を解決するものとして、ジメチレンエーテル型液状フェ
ノール樹脂に０．５ ＰＨＲ以下のフェノールスルホン
酸とＰＨ７以下の無機フィラーを添加することを特徴と
するフェノール樹脂組成物を提供する。すなわち、この
発明においては、フェノール樹脂の増粘をもたらす金属
酸化物やスルホン酸等の従来の酸からなる硬化助剤を使
用することなく、しかも、極少量のフェノールスルホン
酸の添加によって金属や金型の腐食をも回避しつつ、速
硬化性と、常温ライフの延長を実現しようとするもので
ある。[Means for Solving the Problems] This invention solves the above problems by adding phenol sulfonic acid of 0.5 PHR or less and an inorganic filler of PH 7 or less to dimethylene ether type liquid phenol resin. A phenolic resin composition with characteristics is provided. In other words, the present invention does not use curing aids made of conventional acids such as metal oxides or sulfonic acids that cause thickening of phenolic resins, and moreover, by adding a very small amount of phenol sulfonic acid, metals and gold can be cured. The aim is to achieve rapid curing and extended room-temperature life while avoiding corrosion of the mold.
【０００７】まず、この発明では、ジメチレンエーテル
型液状フェノール樹脂として適宜なものを使用すること
ができる。ホルムアルデヒド源とフェノール源とを原料
として使用し、好ましくは触媒を用いて反応させて合成
したものが使用される。この場合のホルムアルデヒド源
としては、ホルムアルデヒド、パラホルムアルデヒド、
ホルムアルデヒド水溶液等を、またフェノール源として
は、フェノーネ、クレゾール、レゾルシン等を用いるこ
とができる。通常、この合成反応は、ホルムアルデヒド
／フェノール原料のモル比として０．３ 〜３．０ 、
好ましくは０．５ 〜２．５ の範囲において、金属の
有機酸塩等を触媒として用いて反応させる。First, in the present invention, any suitable dimethylene ether type liquid phenol resin can be used. It is synthesized by using a formaldehyde source and a phenol source as raw materials, preferably by reacting them using a catalyst. In this case, formaldehyde sources include formaldehyde, paraformaldehyde,
Formaldehyde aqueous solution, etc. can be used, and as a phenol source, phenone, cresol, resorcinol, etc. can be used. Usually, this synthesis reaction uses a formaldehyde/phenol raw material molar ratio of 0.3 to 3.0,
Preferably in the range of 0.5 to 2.5, the reaction is carried out using a metal organic acid salt or the like as a catalyst.
【０００８】触媒としては、酢酸亜鉛、プロピオン酸亜
鉛等の適宜なものが使用される。原料フェノールに対し
て、好ましくは０．１ 〜１．５ ％程度の割合で使用
する。この合成反応の終了後、好ましくは減圧脱水し、
次いで直ちに静置して沈殿物を除去する。脱水条件とし
ては、一般的には、１０〜１００トール程度の真空度に
おいて、脱水最終温度２０〜９０℃程度の温度において
行う。この脱水によって、自由水分２．０ 〜５．０
％程度とするのが好ましい。[0008] As the catalyst, appropriate catalysts such as zinc acetate and zinc propionate are used. It is preferably used in a proportion of about 0.1 to 1.5% based on the raw material phenol. After completion of this synthesis reaction, it is preferably dehydrated under reduced pressure,
Then, it is immediately left to stand to remove the precipitate. The dehydration conditions are generally 10 to 100 torr of vacuum and a final dehydration temperature of 20 to 90°C. This dehydration reduces free water to 2.0 to 5.0
It is preferable to set it to about %.
【０００９】この発明では、このようにして合成された
樹脂に前記した通り０．５ ＰＨＲ以下のフェノールス
ルホン酸を添加混合するが、このフェノールスルホン酸
については、ベンゼン環にアルキル基、水酸基等の置換
基を有していてもよい。より好ましくは、０．０４〜０
．４０ＰＨＲ程度の割合で使用する。０．５ ＰＨＲを
超えてのフェノールスルホン酸の添加は、樹脂の早い増
粘をもたらし、また、金属、金型の腐食の点からも有利
ではない。In the present invention, phenolsulfonic acid of 0.5 PHR or less is added and mixed to the resin thus synthesized as described above, but this phenolsulfonic acid has an alkyl group, a hydroxyl group, etc. on the benzene ring. It may have a substituent. More preferably 0.04 to 0
．． Use at a rate of about 40PHR. Addition of phenolsulfonic acid above 0.5 PHR results in rapid thickening of the resin and is also not advantageous in terms of metal and mold corrosion.
【００１０】また、この発明においては、フェノールス
ルホン酸とともに、ＰＨ７以下の無機フィラーを添加す
る。この無機フィラーとしては、ＳＭＣ、ＢＭＣとして
も有用なガラス繊維とともに使用される、シリカやアル
ミナ等が例示される。この場合、ＰＨ７以下の酸性域、
あるいは中性域にある物質とすることが必要で、ＰＨ７
を超えるものは樹脂の硬化を阻害するので好ましくない
。Further, in the present invention, an inorganic filler having a pH of 7 or less is added together with phenolsulfonic acid. Examples of this inorganic filler include silica and alumina, which are used together with glass fibers that are also useful as SMC and BMC. In this case, an acidic region with a pH of 7 or less,
Alternatively, it is necessary to use a substance in the neutral range, with a pH of 7.
If it exceeds the above range, it is not preferable because it inhibits the curing of the resin.
【００１１】これらの無機フィラーは、重量比でフェノ
ール１００に対して８０〜３００程度で配合するのが好
ましい。さらにまた、この発明の樹脂組成物においては
カップリング剤や離型剤等の他の配合剤を適宜に使用す
ることができる。たとえばシラン系カップリング剤が使
用される。These inorganic fillers are preferably blended in a weight ratio of about 80 to 300 parts per 100 parts of phenol. Furthermore, other compounding agents such as a coupling agent and a mold release agent can be used as appropriate in the resin composition of the present invention. For example, a silane coupling agent is used.
【００１２】以上の通りのこの発明の組成物によって、
従来のフェノール樹脂に比べてはるかに速硬化性で、か
つ、常温ライフの長い樹脂が得られる。その結果、その
成形品の強度も向上する。以下、実施例を示し、さらに
詳しくこの発明の組成物について説明する。[0012] With the composition of the present invention as described above,
A resin that cures much faster than conventional phenolic resins and has a long life at room temperature can be obtained. As a result, the strength of the molded product is also improved. EXAMPLES Hereinafter, the composition of the present invention will be explained in more detail with reference to Examples.
【００１３】[0013]
【実施例】実施例１
ホルムアルデヒド／フェノール原料モル比１．８ 、酢
酸亜鉛の使用量０．９ ％（対フェノール）の条件にお
いて、従来公知の方法と同様に反応させ、反応の終了後
、脱水最終温度７０℃、真空度５０トールで脱水した。
この反応操作によって、自由水分３．０ ％、Ｍｎ３３
０、Ｍｗ４３０、粘度２８００ｃｐｓ ／２５℃の樹脂
を得た。[Example] Example 1 Under the conditions of a formaldehyde/phenol raw material molar ratio of 1.8 and an amount of zinc acetate of 0.9% (based on phenol), a reaction was carried out in the same manner as in a conventionally known method, and after the reaction was completed, dehydration was carried out. Dehydration was carried out at a final temperature of 70° C. and a vacuum degree of 50 Torr. By this reaction operation, free water content was 3.0%, Mn33
0, Mw 430, and viscosity 2800 cps/25°C.
【００１４】この樹脂に、表１に示した通りの配合比に
おいて、すなわち０．３ ＰＨＲのフェノールスルホン
酸と、ＰＨ７以下の無機フィラーとしてのシリカとガラ
ス繊維を混合して組成物とした。この組成物、つまりＢ
ＭＣ材料について成形時間、ライフ、曲げ強度、曲げ弾
性率を評価した。その結果は、表１に示した通り、比較
例に比べて優れたものであった。[0014] This resin was mixed with phenol sulfonic acid of 0.3 PHR, silica as an inorganic filler with a pH of 7 or less, and glass fiber at the compounding ratio shown in Table 1 to prepare a composition. This composition, namely B
The molding time, life, bending strength, and bending modulus of the MC material were evaluated. As shown in Table 1, the results were superior to those of the comparative example.
【００１５】実施例２〜４
実施例１と同様にして配合比を変えて組成物を製造した
。表１に示した通り、その形成材料としての特性は優れ
たものであった。比較例１〜２実施例１と同一の樹脂に
、ＰＨ７以上の水酸化アルミニウムを混合して組成物と
した。Examples 2 to 4 Compositions were produced in the same manner as in Example 1 with different blending ratios. As shown in Table 1, its properties as a forming material were excellent. Comparative Examples 1 to 2 The same resin as in Example 1 was mixed with aluminum hydroxide having a pH of 7 or more to prepare a composition.
【００１６】その成形材料としての特性は、表１に示し
た通り、実施例に比べて劣っていた。As shown in Table 1, its properties as a molding material were inferior to those of the Examples.
【００１７】[0017]
【表１】[Table 1]
【００１８】[0018]
【発明の効果】この発明により、以上詳しく説明した通
り、極小量のフェノールスルホン酸と、ＰＨ７以下の無
機フィラーの添加によって、成形用、各種含浸用、特に
ＳＭＣやＢＭＣに有用な、速硬化性で、常温ライフの長
い液状レゾール型フェノール樹脂組成物が提供される。Effects of the Invention As explained in detail above, the present invention provides a fast-curing property useful for molding and various impregnations, especially SMC and BMC, by adding a very small amount of phenolsulfonic acid and an inorganic filler with a pH of 7 or less. Thus, a liquid resol type phenolic resin composition having a long normal temperature life is provided.
【００１９】この組成物による成形品の強度、成形特性
は良好なものとなる。[0019] The strength and molding properties of molded articles made from this composition are good.
Claims (1)
樹脂に０．５ＰＨＲ以下のフェノールスルホン酸とＰＨ
７以下の無機フィラーを添加配合してなることを特徴と
するフェノール樹脂組成物。[Claim 1] Dimethylene ether type liquid phenol resin with phenol sulfonic acid and pH of 0.5 PHR or less
A phenolic resin composition characterized by containing an inorganic filler of 7 or less.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15072291A JPH04372644A (en) | 1991-06-24 | 1991-06-24 | Phenol resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15072291A JPH04372644A (en) | 1991-06-24 | 1991-06-24 | Phenol resin composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04372644A true JPH04372644A (en) | 1992-12-25 |
Family
ID=15502983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15072291A Pending JPH04372644A (en) | 1991-06-24 | 1991-06-24 | Phenol resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH04372644A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8715543B2 (en) | 2011-03-31 | 2014-05-06 | Ocv Intellectual Capital, Llc | Microencapsulated curing agent |
| US9315655B2 (en) | 2011-12-08 | 2016-04-19 | Ocv Intellectual Capital, Llc | Fiber reinforced resin molding compound and manufacturing method for fiber reinforced resin molded article therefrom |
-
1991
- 1991-06-24 JP JP15072291A patent/JPH04372644A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8715543B2 (en) | 2011-03-31 | 2014-05-06 | Ocv Intellectual Capital, Llc | Microencapsulated curing agent |
| US9725575B2 (en) | 2011-03-31 | 2017-08-08 | Ocv Intellectual Capital, Llc | Microencapsulated curing agent |
| US9315655B2 (en) | 2011-12-08 | 2016-04-19 | Ocv Intellectual Capital, Llc | Fiber reinforced resin molding compound and manufacturing method for fiber reinforced resin molded article therefrom |
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