JP2019210304A - 共重合体、アクリルゴムの製造方法及びアクリルゴム - Google Patents
共重合体、アクリルゴムの製造方法及びアクリルゴム Download PDFInfo
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- JP2019210304A JP2019210304A JP2018104336A JP2018104336A JP2019210304A JP 2019210304 A JP2019210304 A JP 2019210304A JP 2018104336 A JP2018104336 A JP 2018104336A JP 2018104336 A JP2018104336 A JP 2018104336A JP 2019210304 A JP2019210304 A JP 2019210304A
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- 150000003003 phosphines Chemical class 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
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- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
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- 150000004763 sulfides Chemical class 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003497 tellurium Chemical class 0.000 description 1
- QMYDJKWXKHBMIG-UHFFFAOYSA-N tert-butyl 2-methylidenebutanoate Chemical compound CCC(=C)C(=O)OC(C)(C)C QMYDJKWXKHBMIG-UHFFFAOYSA-N 0.000 description 1
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- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
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- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Rigid Pipes And Flexible Pipes (AREA)
- Sealing Material Composition (AREA)
Abstract
Description
前記共重合体はエチレン単量体単位を含有してもよく、前記共重合体中、前記エチレン単量体単位が、前記(メタ)アクリル酸エステル単量体単位100質量部(ただし(メタ)アクリル酸tert−ブチル単量体単位を除く)に対して0.1〜10質量部であってもよい。
前記架橋席単量体単位が、前記架橋性官能基としてカルボキシ基、エポキシ基及びハロゲン基から選ばれる少なくとも1種を有するものであってもよい。
本発明は、前記共重合体を70〜250℃で熱処理する工程を含むアクリルゴムの製造方法を提供する。
前記製造方法において、25℃の水中における酸解離定数(pKa)が5〜−10の酸触媒の存在下で熱処理してもよい。
前記酸触媒がp−トルエンスルホン酸であってもよい。
本発明は、前記製造方法で製造されるアクリルゴムを提供する。
本発明は、前記アクリルゴム100質量部と、カーボンブラック30〜80質量部と、を含むアクリルゴム組成物を提供する。
本発明は、前記アクリルゴム組成物を加硫してなる、圧縮永久歪が27%以下、耐屈曲疲労性が130万回以上の加硫物を提供する。
本発明は、前記加硫物を用いたゴムホースを提供する。
本発明は、前記加硫物を用いたシール部品を提供する。
(メタ)アクリル酸エステル単量体は、アクリルゴムの骨格となるものであり、特に限定されないが、例えば、(メタ)アクリル酸アルキルエステル単量体及び(メタ)アクリル酸アルコキシアルキルエステル単量体が挙げられる。
本実施形態に係るアクリルゴムの製造方法は、上記共重合体を熱処理する工程を含む。熱処理工程を行うことにより、上記熱分解性単量体単位を熱分解してカルボキシ基を有する架橋席単位を生成する。
本実施形態のアクリルゴムは、上記製造方法によって製造される。すなわち、本実施形態のアクリルゴムは、上記共重合体を70〜250℃で熱処理することにより得られる。当該アクリルゴムは、上記熱分解性単量体単位が熱分解されることにより生成された、カルボキシ基を有する架橋席単位を含有する。
本実施形態のアクリルゴム組成物は、上記アクリルゴムと、カーボンブラックと、を含む。上記アクリルゴムを用いることで、得られるアクリルゴム加硫物の機械物性及び耐熱性を向上させることができる。カーボンブラックとしては、特に限定されないが、例えば、アセチレンブラック、ケッチェンブラック、サーマルブラック、チャンネルブラック、ファーネスブラック、ランプブラック及び黒鉛化カーボンブラックなどが挙げられる。機械物性及び耐熱性をより向上させるためには、これらのカーボンブラックのうち、ファーネスブラック及びアセチレンブラックが好ましく、ファーネスブラックがより好ましい。
本実施形態に係るアクリルゴム組成物の加硫物は、上述したアクリルゴム組成物を加硫してなるものである。
<共重合体A>
内容積40リットルの耐圧反応容器に部分ケン化ポリビニルアルコール4質量%の水溶液17kg、酢酸ナトリウム22g、アスコルビン酸56g、エチレンジアミン四酢酸1.12g、硫酸鉄(II)七水和物0.56gを投入し、攪拌機でよく混合しながら槽内上部の空気を窒素で置換後、エチレン0.95kgを槽上部に圧入し、圧力を3.5MPaに調整した。攪拌を続行し、槽内を55℃に保持した後、アクリル酸エチル7.84kg、アクリル酸n−ブチル3.36kg、アクリル酸tert−ブチル168g、tert−ドデシルメルカプタン2.7gのモノマー混合液を6時間かけて圧入した。同時に、別途注入口よりt−ブチルヒドロペルオキシド水溶液(0.25質量%、2リットル)を6時間かけて圧入し、最終重合率95%まで重合を行った。生成した重合液に硼酸ナトリウム水溶液(3.5質量%、7リットル)を凝固剤として添加して重合体を固化し、脱水及び乾燥を行って共重合体Aとした。
共重合体Aと同様な方法であるが、エチレンを圧入せずに重合を行い、共重合体Bを得た。
共重合体Aと同様な方法であるが、アクリル酸tert−ブチルを784gに変更して共重合体Cを得た。
共重合体Aと同様な方法であるが、アクリル酸tert−ブチルを112gに変更し、さらにマレイン酸モノブチルを180g加えて共重合体Dを得た。
共重合体Aと同様な方法であるが、アクリル酸tert−ブチルを112gに変更し、さらにメタクリル酸グリシジルを112g加えて共重合体Eを得た。
共重合体Aと同様な方法であるが、アクリル酸tert−ブチルを2−エチルアクリル酸tert−ブチル205gに変更して共重合体Fを得た。
共重合体Aと同様な方法であるが、アクリル酸tert−ブチルを112gに変更し、さらに2−エチルアクリル酸tert−ブチルを95g加えて共重合体Gを得た。
共重合体Aと同様な方法であるが、アクリル酸エチルを10.4kg、アクリル酸n−ブチルを0.8kgに変更して共重合体Hを得た。
共重合体Aと同様な方法であるが、アクリル酸エチルを2.4kg、アクリル酸n−ブチルを8.9kgに変更して共重合体Iを得た。
共重合体Aと同様な方法であるが、アクリル酸tert−ブチルをマレイン酸モノブチル275gに変更して共重合体Jを得た。
共重合体Aと同様な方法であるが、アクリル酸tert−ブチルをメタクリル酸グリシジル224gに変更して共重合体Kを得た。
共重合体Aと同様な方法であるが、アクリル酸tert−ブチルを1.5kgに変更して共重合体Lを得た。
共重合体Aと同様な方法であるが、アクリル酸tert−ブチルを112gに変更し、さらにマレイン酸モノブチルを1070g加えて共重合体Mを得た。
共重合体Aと同様な方法であるが、アクリル酸tert−ブチルを112gに変更し、さらにメタクリル酸グリシジルを870g加えて共重合体Nを得た。
得られた共重合体の組成は13C NMRを用いて同定した。同定した共重合体の組成は、下記表2及び3に示した。
上述の方法で得た共重合体を、ギヤーオーブン(スガ試験機社製TG−100)を用いて、下記表2及び3に記載した温度及び時間で熱処理し、アクリルゴムを製造した。その後、得られたアクリルゴムを23℃大気中で5時間放冷した。熱処理の工程において下記表2及び3に記載した酸触媒を加える場合は、上述の方法で得た共重合体の乳化液が固化する前に、酸触媒3質量%を共重合体の乳化液に添加して、固化し、脱水及び乾燥を行って共重合体を得た。その後、当該共重合体を上述の手順で熱処理した。
熱処理する前の共重合体と、熱処理した後のアクリルゴムについて、それぞれをトルエンに溶解し、水酸化カリウムを用いた中和滴定カルボキシ基量を測定した。また、熱処理の反応率を、熱処理前後のカルボキシ基量の差を(メタ)アクリル酸tert−ブチル単量体単位及び2−エチルアクリル酸tert−ブチル単量体単位量で除算することにより算出した。
上記の方法で得たアクリルゴムを、下記表1の組成で、0.5L加圧型ニーダーにて15分混練後、6インチオープンロールを用いて20分混練し、アクリルゴム組成物を製造した。なお、表1に記載されている数値の単位は「質量部」である。
・FEFカーボンブラック:東海カーボン社製シーストSO
・ステアリン酸:花王社製ルナックS−90
・4,4’−ビス(α,α−ジメチルベンジル)ジフェニルアミン:アディバント社製ナウガード445(老化防止剤)
・流動パラフィン:カネダ社製ハイコールK−230
・ステアリルアミン:花王社製ファーミン80
・6−アミノヘキシルカルバミド酸:デュポン社製Diak#1(加硫剤)
・1,8−ジアザビシクロ[5.4.0]ウンデカ−7−エン(DBU):ランクセス社製XLA−60(加硫促進剤)
・トリメチルチオ尿素(TMU):大内新興化学工業社製ノクセラーTMU
・1−ベンジル−2−メチルイミダゾール:四国化成工業社製SB−25
・臭化ステアリルトリメチルアンモニウム(STB):東邦化学工業社製カチナールSTB−100
得られたアクリルゴム組成物を厚さ2.4mmのシートに分出しした後、プレス加硫機で170℃、40分間一次加硫をした後、170℃、4時間のギヤーオーブンで二次加硫をして、加硫物を製造した。
得られたアクリルゴム組成物のスコーチタイム、及び加硫物の引張強さ、破断時伸び、硬度、圧縮永久歪及び耐屈曲疲労性を以下の条件で評価し、測定結果を下記表2及び3に示した。
(1)スコーチタイム
JIS K6300:2013に準拠して125℃で測定した。
(2)引張強さ、破断時伸び
JIS K6251:2010に準拠して測定した。
(3)硬度
JIS K6253:2012に準拠してタイプAデュロメータを用いて測定した。
(4)圧縮永久歪
JIS K6262:2013に準拠して測定した。150℃で22時間加熱した場合の圧縮永久歪が27%以内であればシール部品の用途に好適であると判断した。
(5)耐屈曲疲労性(屈曲き裂発生試験)
JIS K6260:2010に準拠して測定した。き裂発生までの屈曲疲労回数が多いほど、耐屈曲疲労性に優れると判断でき、130万回以上であればゴムホース及びシール部品の用途に好適であると判断した。
Claims (11)
- (メタ)アクリル酸エステル単量体単位(ただし(メタ)アクリル酸tert−ブチル単量体単位を除く)と、熱分解性単量体単位としての(メタ)アクリル酸tert−ブチル単量体単位及び2−エチルアクリル酸tert−ブチル単量体単位のうち少なくとも1種と、架橋性官能基を有する架橋席単量体単位と、を含有し、
前記(メタ)アクリル酸エステル単量体単位(ただし(メタ)アクリル酸tert−ブチル単量体単位を除く)100質量部に対して、前記熱分解性単量体単位が0.1〜10質量部であり、前記架橋席単量体単位が5質量部以下である共重合体。 - 前記共重合体がエチレン単量体単位を含有し、
前記共重合体中、前記エチレン単量体単位が、前記(メタ)アクリル酸エステル単量体単位100質量部(ただし(メタ)アクリル酸tert−ブチル単量体単位を除く)に対して0.1〜10質量部である請求項1に記載の共重合体。 - 前記架橋席単量体単位が、前記架橋性官能基としてカルボキシ基、エポキシ基及びハロゲン基から選ばれる少なくとも1種を有する請求項1又は2に記載の共重合体。
- 請求項1〜3のいずれか一項に記載の共重合体を、70〜250℃で熱処理する工程を含む、アクリルゴムの製造方法。
- 25℃の水中における酸解離定数(pKa)が5〜−10の酸触媒の存在下で熱処理する請求項4に記載のアクリルゴムの製造方法。
- 前記酸触媒がp−トルエンスルホン酸である請求項5に記載のアクリルゴムの製造方法。
- 請求項4〜6のいずれか一項に記載の製造方法で製造される、アクリルゴム。
- 請求項7に記載のアクリルゴム100質量部と、カーボンブラック30〜80質量部と、を含むアクリルゴム組成物。
- 請求項8に記載のアクリルゴム組成物を加硫してなる、圧縮永久歪が27%以下、耐屈曲疲労性が130万回以上の加硫物。
- 請求項9に記載の加硫物を用いたゴムホース。
- 請求項9に記載の加硫物を用いたシール部品。
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