JP2565688B2 - Resin composition - Google Patents
Resin compositionInfo
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- JP2565688B2 JP2565688B2 JP61228965A JP22896586A JP2565688B2 JP 2565688 B2 JP2565688 B2 JP 2565688B2 JP 61228965 A JP61228965 A JP 61228965A JP 22896586 A JP22896586 A JP 22896586A JP 2565688 B2 JP2565688 B2 JP 2565688B2
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- resin composition
- oxide
- repeating unit
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Description
【発明の詳細な説明】 ＜産業上の利用分野＞ 本発明は樹脂組成物に関する。詳しくは、ポリフェニ
レンオキシド樹脂とコポリアミド樹脂とを含む樹脂組成
物に関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a resin composition. Specifically, it relates to a resin composition containing a polyphenylene oxide resin and a copolyamide resin.
＜従来の技術＞ ポリフェニレンオキシド樹脂とナイロン６あるいはナ
イロン66等のポリアミド樹脂とから成る樹脂組成物は公
知である（特公昭45−997号公報、特公昭53−47390号公
報、特開昭56−16525号公報、特開昭56−26913号公報等
参照）。これらの樹脂組成物は、両成分樹脂の弱点、例
えば前者の離加工性や低耐溶剤性、後者の低耐熱性や高
吸水性等が改良された有用な樹脂組成物であることが知
られており、近年、自動車外装材等への応用が広がって
いる。<Prior Art> A resin composition composed of a polyphenylene oxide resin and a polyamide resin such as nylon 6 or nylon 66 is known (Japanese Patent Publication No. 45-997, Japanese Patent Publication No. 53-47390, Japanese Patent Publication No. 56-47390). 16525, JP-A-56-26913, etc.). These resin compositions are known to be useful resin compositions in which the weaknesses of the two-component resins, such as the former processability and low solvent resistance, the latter low heat resistance and high water absorption are improved. In recent years, its application to automobile exterior materials and the like is expanding.
＜発明が解決しようとする問題点＞ しかし、ポリフェニレンオキシド樹脂とナイロン６あ
るいは66等のポリアミド樹脂とから成るこれらの樹脂組
成物は吸水性と耐熱性においてまだ十分満足なものとは
いえず、改良が望まれている。本発明の目的は吸水性と
耐熱性が顕著に改良された樹脂組成物を提供することに
ある。<Problems to be Solved by the Invention> However, these resin compositions composed of a polyphenylene oxide resin and a polyamide resin such as nylon 6 or 66 are not yet sufficiently satisfactory in water absorption and heat resistance, and thus improved. Is desired. An object of the present invention is to provide a resin composition having remarkably improved water absorption and heat resistance.
＜問題点を解決するための手段＞ 本発明者らは、ポリフェニレンオキシド樹脂とポリア
ミド樹脂とを含む樹脂組成物について鋭意研究を続けて
きた。その結果、ポリアミド樹脂として特定の構造を有
するコポリアミド樹脂を用いることによって本発明の目
的が達成されることを知見し、本発明を完成させるに至
った。すなわち、本発明は、 ポリフェニレンオキシド樹脂（Ａ）ならびに下記式
〔Ｉ〕の構造で表わされる反復単位と下記式〔II〕の構
造で表わされる反復単位とから成るコポリアミド樹脂
（Ｂ）または下記式〔Ｉ〕の構造で表わされる反復単位
と下記式〔II〕の構造で表わされる反復単位と下記式
〔III〕の構造で表わされる反復単位とから成るコポリ
アミド樹脂（Ｂ）から成る樹脂組成物である。<Means for Solving Problems> The present inventors have conducted extensive studies on a resin composition containing a polyphenylene oxide resin and a polyamide resin. As a result, they have found that the object of the present invention can be achieved by using a copolyamide resin having a specific structure as the polyamide resin, and have completed the present invention. That is, the present invention provides a polyphenylene oxide resin (A) and a copolyamide resin (B) comprising a repeating unit represented by the structure of the following formula [I] and a repeating unit represented by the structure of the following formula [II] or the following formula: A resin composition comprising a copolyamide resin (B) comprising a repeating unit represented by the structure of [I], a repeating unit represented by the structure of the following formula [II] and a repeating unit represented by the structure of the following formula [III]: Is.
−NH（CH2）5CO− 〔II〕 −NH−（CH2）６−NHCO−（CH2）４−CO− 〔III〕 本発明におけるポリフェニレンオキシド樹脂（Ａ）と
は下記一般式〔IV〕 （式中、Ｑはアルキル基、アルコキシ基並びにハロゲン
原子とベンゼン核の間に少くとも２個の炭素原子を有す
るハロゲン化アルキル基およびハロゲン化アルコキシ基
の中から選ばれた１価の置換基、Ｑ′およびＱ″はＱに
関して列挙された置換基、水素原子およびハロゲン原子
の中から選ばれた１員であり、ｎは約50以上の整数であ
る。）で表わされる重合体である。かかるポリフェニレ
ンオキシド樹脂は一般に対応するフェノール誘導体の酸
化重合によって製造される。それらの製造法は例えば特
公昭36−18692号公報、米国特許第3306875号明細書、特
公昭47−36518号公報、米国特許第3787361号明細書、特
公昭60−46129号公報等に記載されている。上記一般式
〔IV〕で表わされるポリフェニレンオキシド樹脂の具体
例としてはポリ（2,6−ジメチル−1,4−フェニレン）オ
キシド、ポリ（2,6−ジエチル−1,4−フェニレン）オキ
シド、ポリ（２−メチル−６−エチル−1,4−フェニレ
ン）オキシド、ポリ（2,6−ジプロピル−1,4−フェニレ
ン）オキシド、ポリ（2,6−ジブチル−1,4−フェニレ
ン）オキシド、ポリ（2,6−ジラウリル−1,4−フェニレ
ン）オキシド、ポリ（2,6−ジメトキシ−1,4−フェニレ
ン）オキシド、ポリ（２−エトキシ−６−ステアリルオ
キシ−1,4−フェニレン）オキシド、ポリ（２−プロポ
キシ−1,4−フェニレン）オキシド、ポリ（2,3,6−トリ
メチル−1,4−フェニレン）オキシド、ポリ（2,6−ジク
ロロ−1,4−フェニレン）オキシド等が挙げられる。こ
れらの中で最も好ましいポリフェニレンオキシド樹脂は
ポリ（2,6−ジメチル−1,4−フェニレン）オキシドであ
る。 -NH (CH 2) 5 CO- (II) -NH- (CH 2) 6 -NHCO- ( CH 2) following general formula and 4 -CO- (III) polyphenylene oxide resin in the present invention (A) [IV ] (In the formula, Q is a monovalent substituent selected from an alkyl group, an alkoxy group, a halogenated alkyl group having at least two carbon atoms between a halogen atom and a benzene nucleus, and a halogenated alkoxy group, Q'and Q "are members selected from the substituents, hydrogen atoms and halogen atoms listed for Q, and n is an integer of about 50 or more." Polyphenylene oxide resins are generally produced by oxidative polymerization of corresponding phenol derivatives, for example, as described in Japanese Patent Publication No. 36-18692, U.S. Pat. No. 3,306,875, Japanese Patent Publication No. 47-36518, and U.S. Pat. No. 3787361, Japanese Patent Publication No. 60-46129, etc. Specific examples of the polyphenylene oxide resin represented by the above general formula [IV] include poly (2,6-dimethyl-1). , 4-phenylene) oxide, poly (2,6-diethyl-1,4-phenylene) oxide, poly (2-methyl-6-ethyl-1,4-phenylene) oxide, poly (2,6-dipropyl-1) , 4-phenylene) oxide, poly (2,6-dibutyl-1,4-phenylene) oxide, poly (2,6-dilauryl-1,4-phenylene) oxide, poly (2,6-dimethoxy-1,4) -Phenylene) oxide, poly (2-ethoxy-6-stearyloxy-1,4-phenylene) oxide, poly (2-propoxy-1,4-phenylene) oxide, poly (2,3,6-trimethyl-1, 4-phenylene) oxide, poly (2,6-dichloro-1,4-phenylene) oxide, etc. Among these, the most preferred polyphenylene oxide resin is poly (2,6-dimethyl-1,4-phenylene). It is an oxide.
本発明におけるコポリアミド樹脂（Ｂ）とは、上記式
〔Ｉ〕で表わされる反復単位と上記式〔II〕で表わされ
る反復単位とからなるコポリアミド樹脂、または上記式
〔Ｉ〕の構造で表わされる反復単位と上記式〔II〕の構
造で表わされる反復単位と上記式〔III〕の構造で表わ
される反復単位とから成るコポリアミド樹脂である。か
かるコポリアミド樹脂の製造法は特公昭59−3871号公
報、特開昭59−161428号公報、特願昭60−126715号明細
書等に記載されている。好ましいコポリアミド樹脂の具
体例としては、ヘキサメチレンジアミン−テレフタル酸
塩とε−カプロラクタムとを共重合して得られる重合体
を挙げることができる。The copolyamide resin (B) in the present invention is a copolyamide resin comprising a repeating unit represented by the above formula [I] and a repeating unit represented by the above formula [II], or a structure represented by the above formula [I]. And a repeating unit represented by the structure of the above formula [II] and a repeating unit represented by the structure of the above formula [III]. A method for producing such a copolyamide resin is described in JP-B-59-3871, JP-A-59-161428, and JP-A-60-126715. Specific examples of preferable copolyamide resin include polymers obtained by copolymerizing hexamethylenediamine-terephthalate and ε-caprolactam.
樹脂組成物の製造法としては従来公知の各種の方法が
採用でき、それらの例としてニーダー、ブラベンダー、
押出機等による溶融混練法、ポリフェニレンオキシド樹
脂の存在下にコポリアミド樹脂の重合を行う方法等が挙
げられる。好ましい方法は溶融混練法である。溶融混練
の方法については例えば特願昭56−26913号公報等に記
載されている。As a method for producing the resin composition, various conventionally known methods can be adopted, examples of which are kneader, Brabender,
Examples thereof include a melt-kneading method using an extruder and the like, a method of polymerizing a copolyamide resin in the presence of a polyphenylene oxide resin, and the like. A preferable method is a melt kneading method. The melt-kneading method is described in, for example, Japanese Patent Application No. 56-26913.
本発明の樹脂組成物は優れた特性を損なわない範囲で
ポリエチレンテレフタレート、ポリブチレンテレフタレ
ート、ポリスチレン、ポリオレフィン等の他の樹脂、ガ
ラス繊維、カーボン繊維等の補強剤、マイカ、タルク等
の充填剤、不飽和化合物、エポキシ化合物等の相溶化
剤、ゴム等の衝撃特性改良剤、安定剤、難燃剤等を含ん
でもよい。The resin composition of the present invention is a resin other than polyethylene terephthalate, polybutylene terephthalate, polystyrene, polyolefin, etc., a reinforcing agent such as glass fiber, carbon fiber, a filler such as mica, talc, etc. within a range that does not impair excellent properties. A compatibilizing agent such as a saturated compound or an epoxy compound, an impact property improving agent such as rubber, a stabilizer, a flame retardant and the like may be contained.
＜実施例＞ 以下、実施例を挙げて本発明を更に詳しく説明する
が、本発明はかかる実施例によりその範囲を限定される
ものではない。なお、実施例中におけるポリフェニレン
オキシド樹脂の還元粘度（ηsp/C）は0.5g/dl濃度のク
ロロホルム溶液について25℃で測定した値であり、コポ
リアミド樹脂の対数粘度（ηinh）は0.5g/dl濃度の濃硫
酸溶液について80℃で測定した値である。また、樹脂組
成物の吸水率（23℃、浸漬飽和）、熱変形温度（HDT、
荷重18.6kg/cm2）、ノッチ付きアイゾット衝撃強度
（NI）、引張強度および伸びはそれぞれASTM法のD570、
D648、D256、D638およびD638によった。また、耐溶剤性
はプラスチックス、第37巻第７号88ページ（1986）に記
載の方法に従って、溶剤が灯油、試験片歪みが１％、温
度／時間が85℃/72時間の条件で試験し、表面状態を観
察することによって判定した。なお、参考例および実施
例中における部は重量部を表わす。<Example> Hereinafter, the present invention will be described in more detail with reference to examples, but the scope of the present invention is not limited by the examples. The reduced viscosity (ηsp / C) of the polyphenylene oxide resin in the examples is a value measured at 25 ° C. for a chloroform solution having a concentration of 0.5 g / dl, and the logarithmic viscosity (ηinh) of the copolyamide resin is 0.5 g / dl. It is a value measured at 80 ° C. for a concentrated sulfuric acid solution having a concentration. In addition, the water absorption of the resin composition (23 ℃, immersion saturation), heat distortion temperature (HDT,
Load 18.6 kg / cm 2 ), notched Izod impact strength (N I ), tensile strength and elongation are respectively ASTM method D570,
According to D648, D256, D638 and D638. Also, solvent resistance is tested according to the method described in Plastics, Vol. 37, No. 7, page 88 (1986) under the conditions of solvent being kerosene, test piece strain of 1%, temperature / time of 85 ° C./72 hours. Then, it was judged by observing the surface condition. The parts in the reference examples and examples represent parts by weight.
参考例１（ポリフェニレンオキシド樹脂の製造。特公昭
60−46129号公報記載の方法に準じた。） 1.5m2の反応器に2,6−ジメチルフェノール122.2kg、
キシレン866.5kg、メタノール1222.2kg、水酸化ナトリ
ウム2.4kg、エリオクロームブラックＴ（半井化学薬品
（株）製）0.55kg、２−ピペコリン1.49kgおよび塩化マ
ンガン四水和物0.099ggを仕込み、撹拌しながら空気を3
00N／分の速度で10時間吹き込み酸化重合せしめた。
この間、反応混合物の温度を30℃、反応系の圧力を8kg/
cm2Gに維持した。反応終了後、常法に従って後処理を行
い、ポリ（2,6−ジメチル−1,4−フェニレン）オキシド
119kgを得た。得られたポリ（2,6−ジメチル−1,4−フ
ェニレン）オキシドの還元粘度は0.541dl/gであった。Reference Example 1 (Production of polyphenylene oxide resin.
According to the method described in JP-A-60-46129. ) 122.2 kg of 2,6-dimethylphenol in a 1.5 m 2 reactor,
866.5 kg of xylene, 1222.2 kg of methanol, 2.4 kg of sodium hydroxide, 0.55 kg of Eriochrome Black T (manufactured by Hanai Chemical Co., Ltd.), 1.49 kg of 2-pipecoline and 0.099 gg of manganese chloride tetrahydrate are charged with stirring. Air 3
It was blown at a rate of 00 N / min for 10 hours for oxidative polymerization.
During this period, the temperature of the reaction mixture was 30 ° C. and the pressure of the reaction system was 8 kg /
It was maintained at cm 2 G. After completion of the reaction, post-treatment was performed according to a conventional method to give poly (2,6-dimethyl-1,4-phenylene) oxide.
I got 119 kg. The reduced viscosity of the obtained poly (2,6-dimethyl-1,4-phenylene) oxide was 0.541 dl / g.
参考例２（コポリアミド樹脂の製造。特願昭60−126715
号明細書記載の方法に準じた。） 撹拌機、窒素導入管、温度計およびガス排気口を備え
た内容積２のオートクレーブ中に、ヘキサメチレンジ
アミン−テレフタル酸塩の50％水溶液、ε−カプロラク
タムおよびヘキサメチレンジアミン−アジピン酸塩の50
％水溶液を第１表の共重合組成のコポリアミド樹脂に対
応する所定の割合で仕込み、撹拌しながら反応混合物の
温度を250℃まで高めた。系内の水分を除いた後、更に2
50〜260℃で１時間撹拌を続けた。その後、反応混合物
を冷却し、重合体（プレポリマー）を取出した。Reference Example 2 (Production of Copolyamide Resin. Japanese Patent Application No. 60-126715
According to the method described in the specification. ) A 50% aqueous solution of hexamethylenediamine-terephthalate, 50% of ε-caprolactam and hexamethylenediamine-adipate were placed in an autoclave with an internal volume of 2 equipped with a stirrer, a nitrogen inlet tube, a thermometer and a gas exhaust port.
% Aqueous solution at a predetermined ratio corresponding to the copolyamide resin having the copolymer composition shown in Table 1, and the temperature of the reaction mixture was raised to 250 ° C. with stirring. After removing the water in the system, 2 more
Stirring was continued for 1 hour at 50-260 ° C. Then, the reaction mixture was cooled and the polymer (prepolymer) was taken out.
ついで、この重合体を粉砕し、よく乾燥した後、ベン
トを有する二軸押出機に供し、連続的に押出しながら温
度320〜330℃、平均滞留時間約10分で反応せしめた。押
出機から押出される重合体をカッティングし、第１表に
示すコポリアミド樹脂のペレットを得た。Then, this polymer was pulverized, dried well, and then subjected to a twin-screw extruder having a vent, and continuously reacted while being extruded at a temperature of 320 to 330 ° C. and an average residence time of about 10 minutes. The polymer extruded from the extruder was cut to obtain pellets of the copolyamide resin shown in Table 1.
実施例１〜２ 参考例１で得られたポリフェニレンオキシド樹脂50部
および参考例２で得られた各種のコポリアミド樹脂50部
をブラベンダープラストグラフを用いて260〜290℃で10
分間混練し、樹脂組成物を製造した。得られた樹脂組成
物から圧縮成形によって作成した各試験片について測定
した物性値を第１表に示す。Examples 1 to 2 50 parts of the polyphenylene oxide resin obtained in Reference Example 1 and 50 parts of the various copolyamide resins obtained in Reference Example 2 were used at 10 ° C. at 260 ° -290 ° C. using a Brabender Plastograph.
Kneading was carried out for a minute to produce a resin composition. Table 1 shows the physical property values measured for each test piece prepared from the obtained resin composition by compression molding.
比較例１ コポリアミド樹脂を市販のナイロン６樹脂（東レ
（株）製アミラン 1007）に替えた以外は実施例１と同
様に混練および圧縮成形し、試験片を得た。これの物性
値を第１表に示す。Comparative Example 1 A copolyamide resin was used as a commercially available nylon 6 resin (Toray
Amilan Co., Ltd. Same as Example 1 except that 1007)
Similarly, kneading and compression molding were performed to obtain a test piece. Physical properties of this
The values are shown in Table 1.
＜発明の効果＞ 本発明によれば、ポリフェニレンオキシド樹脂（Ａ）
とポリアミド樹脂とから成る樹脂組成物において、ポリ
アミド樹脂として前述した特定のコポリアミド樹脂
（Ｂ）を用いることによって、吸水性と耐熱性が顕著に
改良された樹脂組成物を得ることができる。これについ
ては第１表に示した通りであり、ポリアミド樹脂として
ナイロン６を用いた公知の樹脂組成物（比較例１）と比
べて本発明の新規な樹脂組成物（実施例１および２）の
吸水率およびHDTは大幅に改良されている。 <Effect of the Invention> According to the present invention, the polyphenylene oxide resin (A)
By using the above-mentioned specific copolyamide resin (B) as the polyamide resin in the resin composition containing the polyamide resin and the polyamide resin, it is possible to obtain a resin composition having significantly improved water absorption and heat resistance. This is as shown in Table 1, and compared with the known resin composition using nylon 6 as the polyamide resin (Comparative Example 1), the novel resin composition of the present invention (Examples 1 and 2) was used. Water absorption and HDT are greatly improved.
本発明の樹脂組成物は、ポリフェニレンオキシド樹脂
とポリアミド樹脂を含む公知の樹脂組成物と同様の成形
法（射出成形、プレス成形、押出成形等）で成形するこ
とによって、吸水による寸法変化や耐熱性不足による変
形、歪といった不都合に見舞われることなく機械部品、
電気・電子機器部品、自動車部品等、特に耐熱性の要求
される大型部品に適用されることができるのであり、そ
の工業的利用価値はすこぶる大である。The resin composition of the present invention is molded by the same molding method (injection molding, press molding, extrusion molding, etc.) as a known resin composition containing a polyphenylene oxide resin and a polyamide resin, so that dimensional change due to water absorption and heat resistance Machine parts without suffering from inconveniences such as deformation and distortion due to lack,
It can be applied to large-scale parts that require heat resistance, such as electric / electronic device parts and automobile parts, and its industrial utility value is extremely high.
フロントページの続き (72)発明者 西尾 太一 千葉県君津郡袖ヶ浦町北袖２番地 住友 化学工業株式会社内 (56)参考文献 特開 昭62−177065（ＪＰ，Ａ) 国際公開85／5372（ＷＯ，Ａ)Front page continuation (72) Inventor Taichi Nishio, No. 2 Kitasode, Sodegaura-cho, Kimitsu-gun, Chiba Sumitomo Chemical Co., Ltd. (56) Reference JP 62-177065 (JP, A) International Publication 85/5372 (WO, A)
Claims (1)
に下記式〔Ｉ〕の構造で表わされる反復単位と下記式
〔II〕の構造で表わされる反復単位とから成るコポリア
ミド樹脂（Ｂ）または下記式〔Ｉ〕の構造で表わされる
反復単位と下記式〔II〕の構造で表わされる反復単位と
下記式〔III〕の構造で表わされる反復単位とから成る
コポリアミド樹脂（Ｂ）から成る樹脂組成物。 −NH（CH2）5CO− 〔II〕 −NH−（CH2）６−NHCO−（CH2）４−CO− 〔III〕1. A polyphenylene oxide resin (A) and a copolyamide resin (B) comprising a repeating unit represented by the structure of the following formula [I] and a repeating unit represented by the structure of the following formula [II] or the following formula A resin composition comprising a copolyamide resin (B) comprising a repeating unit represented by the structure [I], a repeating unit represented by the structure [II] below, and a repeating unit represented by the structure [III] below. -NH (CH 2) 5 CO- (II) -NH- (CH 2) 6 -NHCO- ( CH 2) 4 -CO- (III)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61228965A JP2565688B2 (en) | 1986-09-26 | 1986-09-26 | Resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61228965A JP2565688B2 (en) | 1986-09-26 | 1986-09-26 | Resin composition |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP554495A Division JPH07233317A (en) | 1995-01-18 | 1995-01-18 | Resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6383162A JPS6383162A (en) | 1988-04-13 |
| JP2565688B2 true JP2565688B2 (en) | 1996-12-18 |
Family
ID=16884640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61228965A Expired - Fee Related JP2565688B2 (en) | 1986-09-26 | 1986-09-26 | Resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2565688B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63113071A (en) * | 1986-10-31 | 1988-05-18 | Mitsubishi Petrochem Co Ltd | Resin composition |
-
1986
- 1986-09-26 JP JP61228965A patent/JP2565688B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6383162A (en) | 1988-04-13 |
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