JP2009242662A - 熱硬化性成型材料 - Google Patents
熱硬化性成型材料 Download PDFInfo
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- JP2009242662A JP2009242662A JP2008092342A JP2008092342A JP2009242662A JP 2009242662 A JP2009242662 A JP 2009242662A JP 2008092342 A JP2008092342 A JP 2008092342A JP 2008092342 A JP2008092342 A JP 2008092342A JP 2009242662 A JP2009242662 A JP 2009242662A
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- 239000012778 molding material Substances 0.000 title claims abstract description 24
- 229920001187 thermosetting polymer Polymers 0.000 title claims abstract description 12
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- 229910002804 graphite Inorganic materials 0.000 claims abstract description 57
- 239000010439 graphite Substances 0.000 claims abstract description 56
- 229920005989 resin Polymers 0.000 claims abstract description 38
- 239000011347 resin Substances 0.000 claims abstract description 38
- -1 phenol compound Chemical class 0.000 claims abstract description 27
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 13
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- 229920001568 phenolic resin Polymers 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
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- 125000005843 halogen group Chemical group 0.000 claims description 3
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- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
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- 235000013539 calcium stearate Nutrition 0.000 description 2
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- 150000001875 compounds Chemical class 0.000 description 2
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Abstract
【解決手段】 縮合多環芳香環を含む芳香環がメチレン鎖を介して架橋結合した基本構造の縮合多環多核芳香族樹脂(I)またはフェノール化合物から誘導のフェノール成分(A)に、それぞれ式(1)のキシリレン成分(B)、式(2)のフェニルメチン成分(C)、および式(3)のメチレン成分(D)が結合した反復単位からなるフェノール系樹脂(II)である樹脂成分に、硬化剤と鱗片状黒鉛と土状黒鉛が分散した複合材料で、鱗片状黒鉛と土状黒鉛を30〜200重量部/樹脂100重量部で含み、鱗片状黒鉛/土状黒鉛の重量比が0/10〜9/1の熱硬化性成型材料。
【化1】
【選択図】 なし
Description
一方、自動車部品やローラ部品の形状が小型部品から大型部品まであり、これらの部品はトランスファー成型等の圧縮成型や射出成型で部品を製造している。
鱗片状黒鉛は射出成型時の圧力により成型体内部に鱗片配向が起こり、熱処理時に成型体内部応力の開放が起因して鱗片配向部の樹脂との接着強度が弱いため成型体内部にクラックが発生していると考えられている。特に大型成型体は小型成型体と比較して内部応力が大きいので大型成型体内部にクラックが発生しやすいと推定される。
クラックを発生した成型材料と成型品は廃棄しなければならず環境負荷の増大、コストアップにつながる。
本発明の目的は、射出成型で成型しても大型成型品内部にクラックが発生しない成型材料を提供することにある。
使用する酸触媒としては、水溶性の酸触媒の場合、架橋剤のヒドロキシメチル基またはハロメチル基と反応し易い有機スルホン酸を使用するか、あるいは原料芳香族化合物と反応するヒドロキシメチル基、ハロメチル基またはホルミル基を有する有機スルホン酸を挙
げることができる。
(a)フェノール化合物に酸触媒の存在下、キシリレングリコールもしくはその反応性誘導体、芳香族アルデヒド、ならびにホルムアルデヒドもしくはその誘導体を反応させる方法。
(b)フェノール化合物に酸触媒の存在下、キシリレングリコールもしくはその反応性誘導体ならびに芳香族アルデヒドを反応させた後、反応混合物を中和してから、2価金属の塩、水酸化物および酸化物、ならびに3価金属の酸化物よりなる群から選ばれた触媒の存在下、ホルムアルデヒドもしくはその誘導体を反応させる方法。
(c)フェノール化合物に2価金属の塩、水酸化物および酸化物、ならびに3価金属の酸化物よりなる群から選ばれた触媒の存在下、ホルムアルデヒドもしくはその誘導体を反応させた後、反応混合物を酸触媒の存在下、キシリレングリコールもしくはその反応性誘導体ならびに芳香族アルデヒドと反応させる方法。
例えば、ペレット状のフェノール系樹脂に固体潤滑剤粉末を硬化剤および所望により他の添加剤と一緒に加え、ミキサー等で予め乾式混合した後、ロール、ニーダー、押出機等の適当な加熱混練装置で樹脂の軟化状態または溶融状態で混練することにより成型材料を製造することができる。
成形温度は約120〜250℃であり、成型温度に応じて数十秒から数時間温度を保持することにより、フェノール系樹脂が不溶不融性の熱硬化物となり、目的とする形状の成形品が得られる。必要に応じて、成型・熱硬化後にポストキュア(後硬化)を施すことで、成型品摺動部品の寸法安定性や耐熱性をさらに向上させることが可能である。この場合、ポストキュア条件は、通常は150〜300℃で1〜40時間である。
(i)COPNA樹脂(エア・ウオーター(株)製:SKレジン−N)
(ii)フェノール系樹脂(エア・ウオーター(株)製:SKレジンQH−B)
硬化剤としてヘキサミンを外数で12%を配合
(iii)鱗片状黒鉛(LONZA社製:グラファイトパウダー、SK−44)
(iv)土状黒鉛(中越黒鉛(株)製:グラファイトパウダー、D−5、)
(v)滑剤(ステアリン酸カルシウム)
上記材料を表1に示す配合割合で予めミキサーを使用して乾式混合した後、100℃にセットされたロール混練機で射出成型材料に適するまで混練して、粉砕機にて造粒し、滑剤(造粒した混練物100重量部に対して0.7部)と造粒した混練物をミキサーにて混合して射出成型材料を調製した。
この射出成型材料を金型温度180℃、射出成型圧力7Mpa、射出時間25秒、硬化時間70秒にセットした射出成型機(東芝製:IR-100GN)で射出成型を行い、直径90mm、高さ80mmの大型成型体を得た。その後180℃で6時間および210℃で12時間の熱処理を行い、得られた成型体の射出方向に成型体の中心部を切断して内部クラックを観察した。結果を表1に示す。
表中内部クラック数は、観察箇所数に対して内部クラックが観察された箇所の割合である。
これに対し、COPNA樹脂およびフェノール系樹脂に対する鱗片状黒鉛と土状黒鉛の配合割合が本発明の範囲外である比較例1〜3では大型成型体の内部クラックが認められた。
したがって、本発明により提供される成型材料は、自動車、OA器機、エアーコンプレッサー等の産業機器などの大型成型品を使用する産業分野に有用である。
Claims (2)
- 縮合多環芳香環を含む芳香環がメチレン鎖を介して架橋結合した基本構造を有する縮合多環多核芳香族樹脂(I)またはフェノール化合物から誘導されたフェノール成分(A)に、それぞれ式(1)で表されるキシリレン成分(B)、式(2)で表されるフェニルメチン成分(C)、および式(3)で表されるメチレン成分(D)が結合した反復単位からなり、[(B)+(C)+(D)]/(A)のモル比が0.4〜0.95で、且つ(D)/[(B)+(C)+(D)]のモル比が0.1〜0.9である数平均分子量500〜5000のフェノール系樹脂(II)のいずれかから選ばれる樹脂成分に、硬化剤と鱗片状黒鉛と土状黒鉛が分散した複合材料であって、樹脂成分100重量部に対して鱗片状黒鉛と土状黒鉛を合計で30〜200重量部を含み、鱗片状黒鉛/土状黒鉛の重量比が0/10〜9/1の範囲内である熱硬化性成型材料。
- 前記鱗片状黒鉛/土状黒鉛の重量比が0/10〜8/2の範囲内であることを特徴とする請求項1に記載の熱硬化性成型材料。
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Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02215854A (ja) * | 1989-02-16 | 1990-08-28 | Ntn Corp | 熱硬化性樹脂組成物 |
JPH0770580A (ja) * | 1993-09-06 | 1995-03-14 | Sumitomo Metal Ind Ltd | 耐揺動性軸受 |
JPH08333474A (ja) * | 1995-06-07 | 1996-12-17 | Kureha Chem Ind Co Ltd | 半導電性樹脂複合材料 |
JPH09302058A (ja) * | 1996-05-20 | 1997-11-25 | Sumikin Chem Co Ltd | 硬化性に優れたフェノール系耐熱樹脂とその製造方法 |
JPH11152319A (ja) * | 1997-11-19 | 1999-06-08 | Sumikin Chemical Co Ltd | フェノール系耐熱樹脂とそれを含む摺動部品用成形材料 |
JP2004204031A (ja) * | 2002-12-25 | 2004-07-22 | Sumitomo Bakelite Co Ltd | フェノール樹脂成形材料 |
JP2005048009A (ja) * | 2003-07-31 | 2005-02-24 | Sumitomo Bakelite Co Ltd | フェノール樹脂成形材料 |
-
2008
- 2008-03-31 JP JP2008092342A patent/JP4900726B2/ja active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH02215854A (ja) * | 1989-02-16 | 1990-08-28 | Ntn Corp | 熱硬化性樹脂組成物 |
JPH0770580A (ja) * | 1993-09-06 | 1995-03-14 | Sumitomo Metal Ind Ltd | 耐揺動性軸受 |
JPH08333474A (ja) * | 1995-06-07 | 1996-12-17 | Kureha Chem Ind Co Ltd | 半導電性樹脂複合材料 |
JPH09302058A (ja) * | 1996-05-20 | 1997-11-25 | Sumikin Chem Co Ltd | 硬化性に優れたフェノール系耐熱樹脂とその製造方法 |
JPH11152319A (ja) * | 1997-11-19 | 1999-06-08 | Sumikin Chemical Co Ltd | フェノール系耐熱樹脂とそれを含む摺動部品用成形材料 |
JP2004204031A (ja) * | 2002-12-25 | 2004-07-22 | Sumitomo Bakelite Co Ltd | フェノール樹脂成形材料 |
JP2005048009A (ja) * | 2003-07-31 | 2005-02-24 | Sumitomo Bakelite Co Ltd | フェノール樹脂成形材料 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015124056A (ja) * | 2013-12-26 | 2015-07-06 | ツバキ山久チエイン株式会社 | 搬送チェーン用の摺動部材 |
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