JP5560765B2 - エチレン−α−オレフィン−非共役ポリエン系共重合体ゴム組成物の製造方法 - Google Patents
エチレン−α−オレフィン−非共役ポリエン系共重合体ゴム組成物の製造方法 Download PDFInfo
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- JP5560765B2 JP5560765B2 JP2010039979A JP2010039979A JP5560765B2 JP 5560765 B2 JP5560765 B2 JP 5560765B2 JP 2010039979 A JP2010039979 A JP 2010039979A JP 2010039979 A JP2010039979 A JP 2010039979A JP 5560765 B2 JP5560765 B2 JP 5560765B2
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- ethylene
- olefin
- copolymer rubber
- polymerization
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- KNBRWWCHBRQLNY-UHFFFAOYSA-N piperidine-1-carbothioylsulfanyl piperidine-1-carbodithioate Chemical compound C1CCCCN1C(=S)SSC(=S)N1CCCCC1 KNBRWWCHBRQLNY-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
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- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
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- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- VMSRVIHUFHQIAL-UHFFFAOYSA-M sodium;n,n-dimethylcarbamodithioate Chemical compound [Na+].CN(C)C([S-])=S VMSRVIHUFHQIAL-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229940052367 sulfur,colloidal Drugs 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
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- 239000003981 vehicle Substances 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
- 229940098697 zinc laurate Drugs 0.000 description 1
- PGNWIWKMXVDXHP-UHFFFAOYSA-L zinc;1,3-benzothiazole-2-thiolate Chemical compound [Zn+2].C1=CC=C2SC([S-])=NC2=C1.C1=CC=C2SC([S-])=NC2=C1 PGNWIWKMXVDXHP-UHFFFAOYSA-L 0.000 description 1
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
- PZKZVLYBWITYEF-UHFFFAOYSA-L zinc;n,n-diethylcarbamothioate Chemical compound [Zn+2].CCN(CC)C([O-])=S.CCN(CC)C([O-])=S PZKZVLYBWITYEF-UHFFFAOYSA-L 0.000 description 1
- LAGTXXPOZSLGSF-UHFFFAOYSA-L zinc;n-butyl-n-phenylcarbamodithioate Chemical compound [Zn+2].CCCCN(C([S-])=S)C1=CC=CC=C1.CCCCN(C([S-])=S)C1=CC=CC=C1 LAGTXXPOZSLGSF-UHFFFAOYSA-L 0.000 description 1
- KMNUDJAXRXUZQS-UHFFFAOYSA-L zinc;n-ethyl-n-phenylcarbamodithioate Chemical compound [Zn+2].CCN(C([S-])=S)C1=CC=CC=C1.CCN(C([S-])=S)C1=CC=CC=C1 KMNUDJAXRXUZQS-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Description
かかる状況のもと、本発明が解決しようとする課題は、低吸水性に優れるゴム発泡体が得られる共重合体ゴム組成物の製造方法を提供することにある。
重合工程(A):
下記一般式(1)で表されるバナジウム化合物と下記一般式(2)で表される有機アルミニウム化合物とを重合触媒成分とする重合触媒の存在下、エチレンとα−オレフィンと非共役ポリエンとを共重合する工程
一般式(1)
VO(OR)mX3-m(式中、Rは炭素原子数1〜8の直鎖状炭化水素基を表し、Xはハロゲン原子を表し、mは0≦m≦3を充足する数を表す。)
一般式(2)
R”jAlX”3-j(式中、R”は炭化水素基を表し、X”はハロゲン原子を表し、jは0<j≦3を充足する数を表す。)
重合工程(B):
下記一般式(3)で表されるバナジウム化合物と下記一般式(4)で表される有機アルミニウム化合物とを重合触媒成分とする重合触媒の存在下、エチレンとα−オレフィンとを共重合、あるいは、エチレンとα−オレフィンと非共役ポリエンとを共重合する工程
一般式(3)
VO(OR’)nX’3-n(式中、R’は炭素原子数3〜8の第2級または第3級炭化水素基を表し、X’はハロゲン原子を表し、nは0<n≦3を充足する数を表す。)
一般式(4)
R'''kAlX'''3-k(式中、R'''は炭化水素基を表し、X'''はハロゲン原子を表し、kは0<k≦3を充足する数を表す。)
下記一般式(1)で表されるバナジウム化合物と下記一般式(2)で表される有機アルミニウム化合物とを重合触媒成分とする重合触媒の存在下、エチレンとα−オレフィンと非共役ポリエンとを共重合する工程
一般式(1)
VO(OR)mX3-m(式中、Rは炭素原子数1〜8の直鎖状炭化水素基を表し、Xはハロゲン原子を表し、mは0≦m≦3を充足する数を表す。)
一般式(2)
R”jAlX”3-j(式中、R”は炭化水素基を表し、X”はハロゲン原子を表し、jは0<j≦3を充足する数を表す。)
下記一般式(3)で表されるバナジウム化合物と下記一般式(4)で表される有機アルミニウム化合物とを重合触媒成分とする重合触媒の存在下、エチレンとα−オレフィンとを共重合、あるいは、エチレンとα−オレフィンと非共役ポリエンとを共重合する工程
一般式(3)
VO(OR’)nX’3-n(式中、R’は炭素原子数3〜8の第2級または第3級炭化水素基を表し、X’はハロゲン原子を表し、nは0<n≦3を充足する数を表す。)
一般式(4)
R'''kAlX'''3-k(式中、R'''は炭化水素基を表し、X'''はハロゲン原子を表し、kは0<k≦3を充足する数を表す。)
一般式(1)
VO(OR)mX3-m(式中、Rは炭素原子数1〜8の直鎖状炭化水素基を表し、Xはハロゲン原子を表し、mは0≦m≦3を充足する数を表す。)
一般式(2)
R”jAlX”3-j(式中、R”は炭化水素基を表し、X”はハロゲン原子を表し、jは0<j≦3を充足する数を表す。)
VOCl3 + m・C2H5OH → VO(OC2H5)mCl3-m + m・HCl
一般式(3)
VO(OR’)nX’3-n(式中、R’は炭素原子数3〜8の第2級または第3級炭化水素基を表し、X’はハロゲン原子を表し、nは0<n≦3を充足する数を表す。)
一般式(4)
R'''kAlX'''3-k(式中、R'''は炭化水素基を表し、X'''はハロゲン原子を表し、kは0<k≦3を充足する数を表す。)
VOCl3 + n・iso-C3H7OH
→ VO(O(iso-C3H7)nCl3-n + n・HCl
(1)エチレン単位量およびプロピレン単位量
共重合体ゴムおよび共重合体ゴム組成物をホットプレス機により厚み約0.1mmのフィルムに成形し、赤外分光光度計(日本分光工業社製 IR−810)により該フィルムの赤外吸収スペクトルを測定した。該赤外吸収スペクトルから、文献(赤外吸収スペクトルによるポリエチレンのキャラクタリゼーション 高山、宇佐美 等著 又は Die Makromolekulare Chemie,177,461(1976)Mc Rae,M.A.,MadamS,W.F.等著)記載の方法に従って、エチレン単位量およびプロピレン単位量を求めた。
共重合体ゴムおよび共重合体ゴム組成物をホットプレス機により厚み約0.5mmのフィルムに成形した。赤外分光光度計により該フィルムの5−エチリデン−2−ノルボルネン由来のピーク(1688cm-1の吸収ピーク)の強度を測定した。該ピーク強度から二重結合のモル含量を求め、該モル含量からヨウ素価を算出した。
ゲル・パーミエイション・クロマトグラフ(GPC)法によって、下記の条件(1)〜(9)で、z平均分子量(Mz)と数平均分子量(Mn)を測定し、分子量分布(Mz/Mn)を求めた。
(1)装置:Waters製150C
(2)分離カラム:昭和電工社製Shodex Packed ColumnA−80M
(3)測定温度:140℃
(4)キャリア:オルトジクロロベンゼン
(5)流量:1.0mL/分
(6)試料濃度:約1mg/1mL
(7)試料注入量:400μL
(8)検出器:示差屈折
(9)分子量標準物質:標準ポリスチレン
ウベローデ型粘度計を用い、135℃のテトラリン溶液中で測定した。
23℃の雰囲気において、長さ50mmに調製したゴム発泡体の空気中での重量と水中に浸漬したときの浮力を測定した。浮力からゴム発泡体の容積を求め、重量/容積により密度を算出した。
長さ50mmに調製したゴム発泡体をASTM D1667に従って測定した。
(共重合体ゴム組成物の調製)
攪拌機を備えたステンレススチール製の第1重合槽に、単位時間・単位重合槽容積あたり、ヘキサンを754g/(hr・L)、エチレン、プロピレンを各々34.4g/(hr・L)、90.5g/(hr・L)の速度で供給した。VOCl3、エタノールを各々59.5mg/(hr・L)、28.6mg/(hr・L)の速度(VOCl3/エタノール=1/1.8(モル比))で、ラインミキサーで混合・攪拌した後に、該重合槽に供給した。また、エチルアルミニウムセスキクロライド(EASC)、水素を各々339.3mg/(hr・L)、0.04NL/(hr・L)の速度で該重合槽に供給した。更に5−エチリデン−2−ノルボルネンを毎時10.05g/(hr・L)の速度で該重合槽に供給した。該重合槽の温度を40℃に保った。該重合槽で、単位時間・単位重合槽容積あたり、43g/(hr・L)の共重合体ゴムが生成した。該共重合体ゴムのエチレン単位量/プロピレン単位量(モル比)は0.65/0.35であり、ヨウ素価は30.9(g/100gポリマー)であった。
第2重合槽から抜き出された重合溶液を分析した結果、共重合体ゴム組成物(以下、EPDM−Aと記す。)の生成量は、単位時間・単位重合槽容積あたり、64g/(hr・L)であり、該共重合体ゴム組成物のエチレン単位量/プロピレン単位量(モル比)は0.73/0.27であり、ヨウ素価は24.8(g/100gポリマー)であり、極限粘度は2.2dl/g、分子量分布は3.6であった。
第2重合槽では、単位時間・単位重合槽容積あたり、21g/(hr・L)の共重合体ゴムが生成し、該共重合体ゴムのエチレン単位量/プロピレン単位量(モル比)は0.88/0.12であり、ヨウ素価は11.9(g/100gポリマー)であることがわかった。
工程−1
100重量部のEPDM−Aと、5重量部の酸化亜鉛(井上石灰社製 メタZ−L102)と、1重量部のステアリン酸と、102重量部のSRFカーボンブラック(旭カーボン社製 旭50HG)、22重量部のタルク(日本タルク社製 ミストロンベーパー)、60重量部のプロセスオイル(出光興産社製 ダイアナPS430)をバンバリーミキサーで混練して、混練物を得た。混練においては、混練開始時のバンバリーミキサーの温度を80℃とし、ローター回転数を60rpmとし、混練時間を5分間とした。
上記混練物と、該混練物中のEPDM−A100重量部あたり、3重量部の酸化カルシウム(井上石灰社製 ベスタPP)、3.4重量部の4,4’−オキシビス(ベンゼンスルホニルヒドラジド)(永和化成社製 ネオセルボンN1000SW)、1.8重量部のアゾジカルボンアミド(永和化成社製 ビニホールAC#3)、0.63重量部のジメチルジチオカルバミン酸亜鉛(ラインケミー社製 レノグランZDMC−80)、1.13重量部のジブチルジチオカルバミン酸亜鉛(ラインケミー社製 レノグランZDBC−80)、0.72重量部のジペンタメチレンチウラムテトラスルフィド(ラインケミー社製 レノグランDPTT−70)、1.88重量部の2−メルカプトベンゾチアゾール(ラインケミー社製 レノグランMBT−80)、1.75重量部の2−メルカプトイミダゾリン(ラインケミー社製 レノグランETU−80)、0.75重量部のモルホリンジスルフィド(大内新興化学社製 ノックマスターR80E)、0.4重量部の2−メルカプトベンゾチアゾール亜鉛塩(川口化学社製 アクセルMZ)、1.2重量部のイオウを、ロール温度50℃の8インチのオープンロールで混合して、共重合体ゴム組成物を得た。
工程−2で得られた共重合体ゴム組成物を、45mmφベント式押出機(中田造機社製 45VAK EXTRUDER)を用いて、幅20mm、厚さ2mmのシートに押出成形した。次に、該シートを230℃の熱空気加硫装置(ミクロ電子社製 HAV)に5分間投入し、発泡と加硫を同時に行って、ゴム発泡体を得た。該発泡体の評価結果を表1に示す。
(共重合体ゴム組成物の調製)
攪拌機を備えたステンレススチール製の第1重合槽に、単位時間・単位重合槽容積あたり、ヘキサンを1118g/(hr・L)、エチレン、プロピレンを各々33.4g/(hr・L)、165.2g/(hr・L)の速度で供給した。VOCl3を60.7mg/(hr・L)の速度で該重合槽に供給した。また、エチルアルミニウムセスキクロライド(EASC)、水素を各々364.4mg/(hr・L)、0.022NL/(hr・L)の速度で該重合槽に供給した。更に5−エチリデン−2−ノルボルネンを毎時8.87g/(hr・L)の速度で該重合槽に供給した。該重合槽の温度を38℃に保った。該重合槽で、単位時間・単位重合槽容積あたり、40g/(hr・L)の共重合体ゴムが生成した。該共重合体ゴムのエチレン単位量/プロピレン単位量(モル比)は0.63/0.37であり、ヨウ素価は24.0(g/100gポリマー)であった。
第2重合槽から抜き出された重合溶液を分析した結果、共重合体ゴム組成物(以下、EPDM−Bと記す。)の生成量は、単位時間・単位重合槽容積あたり、60g/(hr・L)であり、該共重合体ゴム組成物のエチレン単位量/プロピレン単位量(モル比)は0.64/0.36であり、ヨウ素価は23.5(g/100gポリマー)であり、極限粘度は2.0dl/g、分子量分布は2.7であった。
第2重合槽では、単位時間・単位重合槽容積あたり、20g/(hr・L)の共重合体ゴムが生成し、該共重合体ゴムのエチレン単位量/プロピレン単位量(モル比)は0.63/0.37であり、ヨウ素価は22.4(g/100gポリマー)であることがわかった。
EPDM−AにかえてEPDM−Bを用いた以外は、実施例1の「添加剤の配合」および「ゴム発泡体の調製」と同様にして、ゴム発泡体を得た。該発泡体の評価結果を表1に示す。
Claims (3)
- 2つ以上の反応槽が直列に連結した重合反応装置を用いて、連続溶液重合でエチレン−α−オレフィン−非共役ポリエン系共重合体ゴム組成物を製造する方法であって、下記重合工程(A)および重合工程(B)を有することを特徴とするエチレン−α−オレフィン−非共役ポリエン系共重合体ゴム組成物の製造方法。
重合工程(A):
VOCl3、VO(OC2H5)Cl2、VO(OC2H5)0.5Cl2.5、VO(OC2H5)1.5Cl 1.5 、VO(OC2H5)0.8Cl2.2、及びVO(OC2H5)1.8Cl1.2からなる群から選ばれるいずれかのバナジウム化合物と、
下記一般式(2)で表される有機アルミニウム化合物と
を重合触媒成分とする重合触媒の存在下、エチレンとα−オレフィンと非共役ポリエンとを共重合する工程
一般式(2)
R”jAlX”3−j
(式中、R”は炭化水素基を表し、X”はハロゲン原子を表し、jは0<j≦3を充足する数を表す。)
重合工程(B):
VO(O(iso−C3H7))Cl2、VO(O(iso−C3H7))0.5Cl2.5、VO(O(iso−C3H7))1.5Cl 1.5 、及びVO(O(iso−C3H7))0.8Cl2.2からなる群から選ばれるいずれかのバナジウム化合物と、
下記一般式(4)で表される有機アルミニウム化合物と
を重合触媒成分とする重合触媒の存在下、エチレンとα−オレフィンとを共重合、あるいは、エチレンとα−オレフィンと非共役ポリエンとを共重合する工程
一般式(4)
R’’’kAlX’’’3−k(式中、R’’’は炭化水素基を表し、X’’’はハロゲン原子を表し、kは0<k≦3を充足する数を表す。) - 重合工程(A)で製造された共重合体が、エチレンに基づく単量体単位の含有量が40モル%以上70モル%以下、α−オレフィンに基づく単量体単位の含有量が60モル%以下30モル%以上(ただし、エチレンに基づく単量体単位とα−オレフィンに基づく単量体単位との合計を100モル%とする。)であり、ヨウ素価が1以上50以下であるエチレン−α−オレフィン−非共役ポリエン共重合体ゴムであり、
重合工程(B)で製造された共重合体が、エチレンに基づく単量体単位の含有量が70モル%を超え95モル%以下、α−オレフィンに基づく単量体単位の含有量が30モル%未満5モル%以上(ただし、エチレンに基づく単量体単位とα−オレフィンに基づく単量体単位との合計を100モル%とする。)であり、ヨウ素価が0以上50以下であるエチレン−α−オレフィン系共重合体ゴムであり、
重合工程(A)で製造された共重合体ゴムの量と重合工程(B)で製造された共重合体ゴムの量との合計を100重量%として、重合工程(A)で製造された共重合体ゴムの量が40重量%以上90重量%以下であり、重合工程(B)で製造された共重合体ゴムの量が60重量%以下10重量%以上である
ことを特徴とする請求項1に記載のエチレン−α−オレフィン−非共役ポリエン系共重合体ゴム組成物の製造方法。 - α−オレフィンがプロピレンであり、非共役ポリエンが、5−エチリデン−2−ノルボルネン、ジシクロペンタジエンおよび5−ビニル−2−ノルボルネンからなる非共役ポリエン群から選ばれる少なくとも1種の化合物であることを特徴とする請求項1または2に記載のエチレン−α−オレフィン−非共役ポリエン系共重合体ゴム組成物の製造方法。
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