JP6662645B2 - 帯電防止性熱可塑性樹脂組成物およびそれを成形してなる成形体 - Google Patents
帯電防止性熱可塑性樹脂組成物およびそれを成形してなる成形体 Download PDFInfo
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- JP6662645B2 JP6662645B2 JP2016009826A JP2016009826A JP6662645B2 JP 6662645 B2 JP6662645 B2 JP 6662645B2 JP 2016009826 A JP2016009826 A JP 2016009826A JP 2016009826 A JP2016009826 A JP 2016009826A JP 6662645 B2 JP6662645 B2 JP 6662645B2
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- LTXMJHWSYUANCC-UHFFFAOYSA-N tris(2,4-ditert-butyl-5-methylphenyl) phosphite Chemical compound C1=C(C(C)(C)C)C(C)=CC(OP(OC=2C(=CC(=C(C)C=2)C(C)(C)C)C(C)(C)C)OC=2C(=CC(=C(C)C=2)C(C)(C)C)C(C)(C)C)=C1C(C)(C)C LTXMJHWSYUANCC-UHFFFAOYSA-N 0.000 description 1
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- DECPGQLXYYCNEZ-UHFFFAOYSA-N tris(6-methylheptyl) phosphite Chemical compound CC(C)CCCCCOP(OCCCCCC(C)C)OCCCCCC(C)C DECPGQLXYYCNEZ-UHFFFAOYSA-N 0.000 description 1
- JZNDMMGBXUYFNQ-UHFFFAOYSA-N tris(dodecylsulfanyl)phosphane Chemical compound CCCCCCCCCCCCSP(SCCCCCCCCCCCC)SCCCCCCCCCCCC JZNDMMGBXUYFNQ-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
- 239000004762 twaron Substances 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- DQWFTGPZPKZMAB-UHFFFAOYSA-N undecane-1,6,11-triamine Chemical compound NCCCCCC(N)CCCCCN DQWFTGPZPKZMAB-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
Description
前記高分子化合物(A)が、ジオール、脂肪族ジカルボン酸、および芳香族ジカルボン酸から構成されるポリエステル(E)と、下記一般式(1)、
で表される基を一つ以上有し、両末端に水酸基を有する化合物(C)と、反応性官能基を有する化合物(D)とが、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有することを特徴とするものである。
(式(2)中、R1は水素原子、ヒドロキシ基、炭素原子数1〜30の直鎖または分岐を有するアルキル基、ヒドロキシアルキル基、アルコキシ基、ヒドロキシアルコキシ基またはオキシラジカルを表し、R2は、直鎖または分岐を有する炭素原子数1〜31の脂肪族炭化水素基、または、下記一般式(3)で表される置換基を表し、nは1〜4の整数を表すが、R2が一般式(3)で表される置換基である場合、nは1を表す。)
(式(3)中、R1は、式(2)と同じものを表す。)
(式(4)中、R1は、式(2)と同じものを表す。)
(式(5)中、R1は、式(2)と同じものを表し、Yは、直接結合またはメチレン基を表し、rは1〜20の整数を表す。)
(式(6)中、R1は、式(2)と同じものを表し、R3は、直鎖または分岐を有する炭素原子数1〜31のアルキル基、直鎖または分岐を有する炭素原子数2〜31のアルケニル基、2,2,6,6−テトラメチルピペリジル基、または、1,2,2,6,6−ペンタメチルピペリジル基を表し、sは2〜20の整数を表す。)
(式(7)中、uは、2〜20の数を表す。)で表される化合物からなる群から選ばれる少なくとも一種であることが好ましい。
(式(8)中のR4およびR5は、各々独立して、水素原子、塩素原子、または、直鎖または分岐を有する炭素原子数1〜4のアルキル基を表し、R6およびR7は、各々独立して、水素原子、または、直鎖または分岐を有する炭素原子数1〜18のアルキル基、炭素原子数1〜18のヒドロキシアルキル基、炭素原子数1〜18のアルコキシ基、炭素原子数1〜18のヒドロキシアルコキシ基、炭素原子数7〜30のアルキルアリール基を表し、R8、R9は各々独立に、水素原子、または、直鎖または分岐を有する炭素原子数1〜4のアルキル基を表す。)、
(式(9)中のR10は、式(8)のR4と同じものを表し、R12、R13は各々独立に、水素原子、直鎖または分岐を有する炭素原子数1〜18のアルキル基、炭素原子数1〜18のヒドロキシアルキル基、炭素原子数1〜18のアルコキシ基、炭素原子数1〜18のヒドロキシアルコキシ基、炭素原子数7〜30のアルキルアリール基、炭素原子数7〜30のアリールアルキル基、炭素原子数3〜20のアルケニル基、および炭素原子数9〜20のN−アルキレンシクロヘキセン−1,2−ジカルボイミド基を表し、kは1または2を表し、kが1の場合、R11は、水素原子、直鎖または分岐を有する炭素原子数1〜18のアルキル基、炭素原子数1〜18のヒドロキシアルキル基、炭素原子数1〜18のアルコキシ基、炭素原子数1〜18のヒドロキシアルコキシ基、炭素原子数7〜30のアルキルアリール基、炭素原子数7〜30のアリールアルキル基、炭素原子数3〜20のアルケニル基、および炭素原子数9〜20のN−アルキレンシクロヘキセン−1,2−ジカルボイミド基を表し、kが2の場合、R11は、炭素原子数1〜20のアルカンジイル基を表し、R11、R12およびR13のアルキル基、ヒドロキシアルキル基、アルコキシ基、ヒドロキシアルコキシ基、アルキルアリール基、アリールアルキル基、アルケニル基およびアルカンジイル基中のメチレン基が、エチレングリコール、プロピレングリコール、−O−、−CO−、−OCO−、−COO−で置換されていてもよい。)
(式(10)中のR14は、直鎖または分岐を有する炭素原子数1〜20のアルキル基、炭素原子数3〜8のシクロアルキル基、炭素原子数3〜20のアルケニル基、炭素原子数6〜20のアリール基、炭素原子数7〜30のアルキルアリール基または炭素原子数7〜30のアリールアルキル基を表し、R15は水素原子、直鎖または分岐を有する炭素原子数1〜8のアルキル基または炭素原子数3〜8のアルケニル基を表し、R16は水素原子、ヒドロキシ基、炭素原子数1〜8のアルキル基、または、−O−R14を表し、R17は水素原子、炭素原子数1〜8のアルキル基、−O−R14または炭素原子6〜20のアリール基を表し、R14〜R17のアルキル基、アルケニル基、アルキルアリール基、アリールアルキル基中のメチレン基およびシクロアルキル基の環状構造を形成する炭素原子が、−O−、−S−、−CO−、−O−CO−、−CO−O−、―NR’−で置き換わっていてもよく、アルキル基、シクロアルキル基、アルケニル基、アリール基、アルキルアリール基およびアリールアルキル基の水素原子が、ヒドロキシ基、ハロゲン原子、炭素原子数1〜12のアルキル基、または炭素原子数1〜12のアルコキシ基で置換されていてもよく、R’は、水素原子または炭素原子数1〜18のアルキル基を表し、複数のR14,R15,R16およびR17は、各々、同一であってもよく、異なるものであってもよい)
(式(11)中のR18は、水素原子、ヒドロキシ基、直鎖または分岐を有する炭素原子数1〜8のアルキル基を表わし、複数のR18は、各々異なるものであってもよく、同一であってもよい。wは4〜14の数を表す。)
(式(12)中のR19、R20およびR21は各々独立に、水素原子、塩素原子、ヒドロキシ基、カルボキシル基、直鎖または分岐を有する炭素原子数1〜18のアルキル基、炭素原子数1〜18のヒドロキシアルキル基、炭素原子数1〜18のアルコキシ基、炭素原子数1〜18のヒドロキシアルコキシ基、炭素原子数7〜30のアルキルアリール基、炭素原子数7〜30のアルコキシアリール基、アセトフェノン、炭素原子数4〜15のアクリロイルオキシアルコキシ基または炭素原子数5〜15のメタクリロイルオキシアルコキシ基、ヒドロキシベンゾフェノキシアルキルオキシ基を表し、R22、R23は各々独立に、水素原子、塩素原子、ヒドロキシ基、スルホニル基、ナトリウムスルホニル基、ヒドロキシスルホニル基、アクリロイルオキシアルコキシ基を表す。)で表される化合物からなる群のうち1種以上であることが好ましい。
で表される基を一つ以上有し、両末端に水酸基を有する化合物(C)、および、反応性官能基を有する化合物(D)が、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有している。
本発明の樹脂組成物において利用可能な樹脂は、熱可塑性樹脂であれば制限はないが、帯電防止性能の持続性と成形性の観点から、特に、ポリオレフィン系樹脂、スチレン系樹脂、ポリエステル系樹脂、ポリエーテル系樹脂、ポリカーボネート系樹脂、ポリアミド系樹脂、含ハロゲン樹脂が好ましい。
高分子化合物(A)は、樹脂組成物に帯電防止性を付与するために配合される。本発明で用いる高分子化合物(A)は、ジオールと、脂肪族ジカルボン酸と、芳香族ジカルボン酸と、下記一般式(1)で表される基を一つ以上有し、両末端に水酸基を有する化合物(C)と、反応性官能基を有する化合物(D)とが、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有している。
化合物(C)は、親水性を有する化合物が好ましく、上記一般式(1)で示される基を有するポリエーテルがより好ましく、下記一般式(13)で表されるポリエチレングリコールが特に好ましい。
本発明において反応性官能基を有する化合物(D)は、カルボキシル基とエステル結合を介して結合するもの、またはアミド結合を介して結合できるものであればよく、ポリエステル(E)、および化合物(C)と、エステル結合またはアミド結合を介して結合しうるもの、あるいは、ポリエステル(E)から構成されたブロック、および化合物(C)から構成されたブロックがエステル結合を介して繰り返し交互に結合してなる両末端にカルボキシル基を有するブロックポリマー(G)と、エステル結合またはアミド結合を介して結合し得るものであればよい。かかる官能基としては、エポキシ基、水酸基、アミノ基等が挙げられる。
上述のとおり、本発明の樹脂組成物においては、高分子化合物(A)は、帯電防止性の観点から、ジオール、脂肪族ジカルボン酸および芳香族ジカルボン酸から構成されるポリエステル(E)、化合物(C)、および反応性官能基を有する化合物(D)が、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有することが好ましい。
本発明に係る両末端にカルボキシル基を有する構造のブロックポリマー(G)は、ポリエステル(E)から構成されたブロックと、化合物(C)から構成されたブロックとを有し、これらのブロックが、カルボキシル基と水酸基とにより形成されたエステル結合を介して繰り返し交互に結合してなる構造を有する。かかるブロックポリマー(G)の一例を挙げると、例えば、下記一般式(14)で表される構造を有するものが挙げられる。
本発明の樹脂組成物において使用可能なヒンダードアミン化合物(B)は、2,2,6,6−テトラメチルピペリジルの構造を有する化合物が挙げられ、具体的には、例えば、2,2,6,6−テトラメチル−4−ピペリジルステアレート、1,2,2,6,6−ペンタメチル−4−ピペリジルステアレート、2,2,6,6−テトラメチル−4−ピペリジルベンゾエート、ビス(2,2,6,6−テトラメチル−4−ピペリジル)セバケート、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)セバケート、ビス(2,2,6,6−テトラメチル−1−(オクチルオキシ)ピペリジル−4−イル)セバケート、メチル(1、2,2,6,6−ペンタメチル−4−ピペリジル)セバケート、ブタン−1,2,3,4−テトラカルボン酸テトラキス(2,2,6,6−テトラメチル−4−ピペリジニル)、ブタン−1,2,3,4−テトラカルボン酸テトラキス(1,2,2,6,6−ペンタメチル−4−ピペリジニル)、ビス(2,2,6,6−テトラメチル−4−ピペリジル)・ジ(トリデシル)−1,2,3,4−ブタンテトラカルボキシレート、ビス(1,2,2,6,6−ペンタメチル−4−ピペリジル)・ジ(トリデシル)−1,2,3,4−ブタンテトラカルボキシレート、ビス(1,2,2,4,4−ペンタメチル−4−ピペリジル)−2−ブチル−2−(3,5−ジ第三ブチル−4−ヒドロキシベンジル)マロネート、1−(2−ヒドロキシエチル)−2,2,6,6−テトラメチル−4−ピペリジノ−ル/コハク酸ジエチル重縮合物、1,6−ビス(2,2,6,6−テトラメチル−4−ピペリジルアミノ)ヘキサン/2,4−ジクロロ−6−モルホリノ−s−トリアジン重縮合物、1,6−ビス(2,2,6,6−テトラメチル−4−ピペリジルアミノ)ヘキサン/2,4−ジクロロ−6−第三オクチルアミノ−s−トリアジン重縮合物、セバシン酸1−メチル−10−(1,2,2,6,6−ペンタメチル−4−ピペリジル)およびビス(2,2,6,6−テトラメチル−4−ピペリジル)セバケートの重縮合物、ブタンテトラカルボン酸テトラメチルエステル,スピログリコールおよびN−メチルピペリジノールとのエステル、ブタンテトラカルボン酸、3−ヒドロキシ−2,2−ジメイツペンタナールおよびN−メチルピペリジノールとのエステルの重縮合物、1,2,3,4−ブタンテトラカルボン酸テトラメチルエステル、2,2,6,6−テトラメチル−4−ピペリジノールおよびβ,β,β’,β’−テトラメチル−2,4,8,10−テトラオキサスピロ[5.5]ウンデカン−3,9−ジエタノールの重縮合物、2,4−ジクロロ−6−(1,1,3,3−テトラメチルブチルアミノ)−1,3,5−トリアジン−N,N’−ビス(2,2,6,6−テトラメチル−4−ピペリジル)ヘキサメチレンジアミン重縮合物、2,4−ジクロロ−6−(1,1,3,3−テトラメチルブチルアミノ)−1,3,5−トリアジン、1,5,8,12−テトラキス〔2,4−ビス(N−ブチル−N−(2,2,6,6−テトラメチル−4−ピペリジル)アミノ)−s−トリアジン−6−イル〕−1,5,8,12−テトラアザドデカン、1,5,8,12−テトラキス〔2,4−ビス(N−ブチル−N−(1,2,2,6,6−ペンタメチル−4−ピペリジル)アミノ)−s−トリアジン−6−イル〕−1,5,8−12−テトラアザドデカン、1,6,11−トリス〔2,4−ビス(N−ブチル−N−(2,2,6,6−テトラメチル−4−ピペリジル)アミノ)−s−トリアジン−6−イル〕アミノウンデカン、1,6,11−トリス〔2,4−ビス(N−ブチル−N−(1,2,2,6,6−ペンタメチル−4−ピペリジル)アミノ)−s−トリアジン−6−イル〕アミノウンデカン、ビス{4−(1−オクチルオキシ−2,2,6,6−テトラメチル)ピペリジル}デカンジオナート、ビス{4−(2,2,6,6−テトラメチル−1−ウンデシルオキシ)ピペリジル)カーボナート、BASF社製商品名「CHIMASSORB119」、BASF社製商品名「CHIMASSORB944」、BASF社製商品名「CHIMASSORB2020」、BASF社製商品名「TINUVIN XT850}、BASF社製TINUVIN NOR 371、株式会社ADEKA製商品名の「アデカスタブLA−77」、「アデカスタブLA−94」、「アデカスタブLA−402XP」「アデカスタブLA−402AF」、「アデカスタブLA−40MP」、「アデカスタブLA−502XP」等が挙げられる。
(1)イミダゾリニウムカチオン
炭素原子数5〜15のものが挙げられ、例えば、1,2,3,4−テトラメチルイミダゾリニウム、1,3−ジメチルイミダゾリニウム;
(2)イミダゾリウムカチオン
炭素原子数5〜15のものが挙げられ、例えば、1,3−ジメチルイミダゾリウム、1−エチル−3−メチルイミダゾリウム;
(3)テトラヒドロピリミジニウムカチオン
炭素原子数6〜15のものが挙げられ、例えば、1,3−ジメチル−1,4,5,6−テトラヒドロピリミジニウム、1,2,3,4−テトラメチル−1,4,5,6−テトラヒドロピリミジニウム;
(4)ジヒドロピリミジニウムカチオン
炭素原子数6〜20のものが挙げられ、例えば、1,3−ジメチル−1,4−ジヒドロピリミジニウム、1,3−ジメチル−1,6−ジヒドロピリミジニウム、8−メチル−1,8−ジアザビシクロ[5,4,0]−7,9−ウンデカジエニウム、8−メチル−1,8−ジアザビシクロ[5,4,0]−7,10−ウンデカジエニウム。
(1)イミダゾリニウム骨格を有するグアニジニウムカチオン
炭素原子数8〜15のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチルイミダゾリニウム、2−ジエチルアミノ−1,3,4−トリメチルイミダゾリニウム;
(2)イミダゾリウム骨格を有するグアニジニウムカチオン
炭素原子数8〜15のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチルイミダゾリウム、2−ジエチルアミノ−1,3,4−トリメチルイミダゾリウム;
(3)テトラヒドロピリミジニウム骨格を有するグアニジニウムカチオン
炭素原子数10〜20のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチル−1,4,5,6−テトラヒドロピリミジニウム、2−ジエチルアミノ−1,3−ジメチル−4−エチル−1,4,5,6−テトラヒドロピリミジニウム;
(4)ジヒドロピリミジニウム骨格を有するグアニジニウムカチオン
炭素原子数10〜20のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチル−1,4−ジヒドロピリミジニウム、2−ジメチルアミノ−1,3,4−トリメチル−1,6−ジヒドロピリミジニウム、2−ジエチルアミノ−1,3−ジメチル−4−エチル−1,4−ジヒドロピリミジニウム、2−ジエチルアミノ−1,3−ジメチル−4−エチル−1,6−ジヒドロピリミジニウム。
本発明の成形体は、本発明の樹脂組成物が成形されてなるものである。本発明の樹脂組成物を成形することにより、持続性を有した充分な帯電防止性と長期の光安定性を有する成形品を製造することができる。成形方法としては、特に限定されるものではなく、押出加工、カレンダー加工、射出成形、ロール、圧縮成形、ブロー成形、回転成形等が挙げられ、樹脂板、シート、フィルム、ボトル、繊維、異形品等の種々の形状の成形品が製造できる。
下記の製造例に従い、高分子化合物(A)を製造した。また、下記の製造例において数平均分子量は、下記の方法で測定した。
数平均分子量(以下、「Mn」と称する)は、ゲルパーミエーションクロマトグラフィー(GPC)法によって測定した。Mnの測定条件は以下の通りである。
装置 :日本分光株式会社製GPC装置
溶媒 :テトラヒドロフラン
基準物質 :ポリスチレン
検出器 :示差屈折計(RI検出器)
カラム固定相 :昭和電工株式会社製Shodex KF−804L
カラム温度 :40℃
サンプル濃度 :1mg/1mL
流量 :0.8mL/min.
注入量 :100μL
セパラブルフラスコに、ジオールとして、1,4−シクロヘキサンジメタノールを656g(4.55モル)、脂肪族ジカルボン酸として、アジピン酸を708g(4.85モル)、芳香族ジカルボン酸として、無水フタル酸を0.7g(4.73×10−3モル)、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン;株式会社ADEKA製商品名「アデカスタブAO−60」)を0.7g仕込み、160℃から210℃まで徐々に昇温しながら常圧で5時間、その後210℃、減圧下で3時間重合してポリエステル(E)−1を得た。ポリエステル(E)−1の酸価は28、数平均分子量Mnはポリスチレン換算で5,400であった。
セパラブルフラスコに、ジオールとして、1,4−ビス(β−ヒドロキシエトキシ)ベンゼンを370g(1.87モル)、脂肪族ジカルボン酸として、アジピン酸を289g(1.98モル)、芳香族ジカルボン酸として、イソフタル酸を8g(0.05モル)、酸化防止剤(アデカスタブAO−60)を0.5g仕込み、180℃から220℃まで徐々に昇温しながら常圧で5時間重合した。その後、テトライソプロポキシチタネートを0.5g仕込み、220℃、減圧下で5時間重合して、ポリエステル(E)−2を得た。ポリエステル(E)−2の酸価は56、数平均分子量Mnは、ポリスチレン換算で4,900であった。
セパラブルフラスコに、ジオールとして、ビスフェノールAのエチレンオキサイド付加物を591g、脂肪族ジカルボン酸として、セバシン酸を235g(1.16モル)、芳香族ジカルボン酸として、イソフタル酸を8g(0.05モル)、一般式(1)で表される基を一つ以上有し両末端に水酸基を有する化合物(C)として、数平均分子量2,000のポリエチレングリコール(C)−2を300g、酸化防止剤(アデカスタブAO−60)を0.8g仕込み、180℃から220℃まで徐々に昇温しながら常圧で5時間重合した。その後、テトライソプロポキシチタネートを0.6g仕込み、220℃、減圧下で7時間重合して、両末端にカルボキシルを有するブロックポリマー(G)−3を得た。このブロックポリマー(G)−3の酸価は10、数平均分子量Mnはポリスチレン換算で10,100であった。
下記の表1〜9に記載した配合量(質量部)に基づいてブレンドした樹脂組成物を用いて、下記に示す試験片作製条件に従い、試験片を得た。得られた試験片を用いて、下記の方法で、表面固有抵抗値(SR値)の測定、耐水拭き性試験を行った。
熱可塑性樹脂1を59質量部、高分子化合物(A)として(A)−1を41質量部、フェノール系酸化防止剤(株式会社ADEKA製商品名「アデカスタブAO−60」)0.1質量部、リン系酸化防止剤(株式会社ADEKA製商品名「アデカスタブ2112」)0.05質量部、ステアリン酸カルシウム0.05質量、ヒンダードアミン化合物(B)としてLA−52を0.4質量部、および、紫外線吸収剤(H)としてLA−36を0.4質量部ブレンドした樹脂組成物を用いて、下記の試験片作成条件に従って製造したところ、成形加工性が悪いため試験片を作成できなかった。
熱可塑性樹脂1を90質量部、高分子化合物(A)として(A)−1を10質量部、フェノール系酸化防止剤(株式会社ADEKA製商品名「アデカスタブAO−60」)0.1質量部、リン系酸化防止剤(株式会社ADEKA製商品名「アデカスタブ2112」)0.05質量部、ステアリン酸カルシウム0.05質量、ヒンダードアミン化合物(B)としてLA−52を6質量部、および、紫外線吸収剤(H)LA−36を0.4質量部ブレンドした樹脂組成物を用いて、下記の試験片作成条件に従って試験片を作成したところ、試験片の表面からブリードアウトが確認されたため、下記の評価を実施しなかった。
熱可塑性樹脂1を90質量部、高分子化合物(A)として(A)−1を10質量部、フェノール系酸化防止剤(株式会社ADEKA製商品名「アデカスタブAO−60」)0.1質量部、リン系酸化防止剤(株式会社ADEKA製商品名「アデカスタブ2112」)0.05質量部、ステアリン酸カルシウム0.05質量、ヒンダードアミン化合物(B)としてLA−52を0.4質量部、および、紫外線吸収剤(H)LA−36を11質量部ブレンドした樹脂組成物を用いて、下記の試験片作成条件に従って試験片を作成したところ、試験片の表面からブリードアウトが確認されたため、下記の評価を実施しなかった。
フェノール系酸化防止剤(株式会社ADEKA製商品名「アデカスタブAO−60」)0.1質量部、リン系酸化防止剤(株式会社ADEKA製商品名「アデカスタブ2112」)0.05質量部、ステアリン酸カルシウム0.05質量、および、下記の表1〜9中に示す配合量に基づいてブレンドした樹脂組成物を、(株)池貝製の二軸押出機(PCM30,60mesh入り)を用いて、230℃、9kg/時間の条件で造粒し、ペレットを得た。得られたペレットを、横型射出成形機(NEX80:日精樹脂工業(株)製)を用い、樹脂温度230℃、金型温度50℃の加工条件で成形し、表面固有抵抗値測定用試験片(100mm×100mm×3mm)および耐候試験用試験片(60mm×30mm×2mm)を得た。
熱可塑性樹脂2;高密度ポリエチレン(メルトフローレート=7g/10min)日本ポリエチレン株式会社製、商品名 ノバテックHD HJ560
熱可塑性樹脂3;耐衝撃性ポリスチレン(メルトフローレート=2.7g/10min)東洋スチレン株式会社製、商品名 E640N
NaDBS;ドデシルベンゼンスルホン酸ナトリウム
LiOTs;p−トルエンスルホン酸リチウム
比較化合物1;グリセリンモノステアレート
比較化合物2;ポリエーテルポリオレフィンブロック共重合体、三洋化成工業株式会社製商品名 「ペレスタット300」
LA−52:ブタン−1,2,3,4−テトラカルボン酸テトラキス(1,2,2,6,6−ペンタメチル−4−ピペリジニル)
622:一般式(7)で表される化合物 BASF社製商品名(Tinuvin622)
LA−57:ブタン−1,2,3,4−テトラカルボン酸テトラキス(2,2,6,6−テトラメチル−4−ピペリジニル)
LA−81:ビス{4−(2,2,6,6−テトラメチル−1−ウンデシルオキシ)ピペリジル}カーボナート
LA−77:ビス(2,2,6,6−テトラメチル−4−ピペリジルセバケート)
LA−63P:ブタンテトラカルボン酸テトラメチルエステル,スピログリコールおよびN−メチルピペリジノールとのエステルおよびブタンテトラカルボン酸、3−ヒドロキシ−2,2−ジメイツペンタナールおよびN−メチルピペリジノールとのエステルの重縮合物
LA−68:1,2,3,4−ブタンテトラカルボン酸テトラメチルエステル、2,2,6,6−テトラメチル−4−ピペリジノールおよびβ,β,β’,β’−テトラメチル−2,4,8,10−テトラオキサスピロ[5.5]ウンデカン−3,9−ジエタノールの重縮合物
LA−94G:2,4−ジクロロ−6−(1,1,3,3−テトラメチルブチルアミノ)−1,3,5−トリアジン−N,N’−ビス(2,2,6,6−テトラメチル−4−ピペリジル)ヘキサメチレンジアミン重縮合物
LA−402AF:株式会社ADKEA製商品名「アデカスタブLA−402AF」(マスターバッチ)
LA−502XP:株式会社ADKEA製商品名「アデカスタブLA−502XP」(マスターバッチ)
LA−36:2−(2’−ヒドロキシ−3’−tert−ブチル−5’−メチルフェニル)−5−クロロベンゾトリアゾール
LA−29:2−(2H−ベンゾトリアゾール−2−イル)−4−(1,1,3,3−テトラメチルブチル)フェノール
1413:2−ヒドロキシ−4−n−オクチルオキシベンゾフェノン
1164:2−(4,6−ビス−(2,4−ジメチルフェニル)−1,3,5−トリアジン−2−イル)−5−(オクチルオキシ)−フェノール
LA−31:2,2’−メチレンビス[6−(ベンゾトリアゾール−2−イル)−4−tert−オクチルフェノール]
LA−32:2−(2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール
234:2−(3’,5’−ビス(1−メチル−1−フェニルエチル)−2’−ヒドロキシフェニル)ベンゾトリアゾール
LA−46:2−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−5−[2−(2−エチルヘキサノイルオキシ)エトキシ]−フェノール
LA−F70:2,4,6−トリス(2−ヒドロキシ−4−ヘキシルオキシ−3−メチルフェニル)−1,3,5−トリアジン
UVA1:ビス(2−(4−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−3−ヒドロキシフェノキシ)エチル)ドデカンジオエート
1577:2−(4,6−ジフェニル−1,3,5−トリアジン−2−イル)−5−(ヘキシル)オキシフェノール
110:2−ヒドロキシ−4−メトキシベンゾフェノン
得られた表面固有抵抗値測定用試験片(100mm×100mm×3mm)を、成形加工後直ちに、温度25℃、湿度60%RHの条件下に保存し、成形加工の1日および30日保存後に、同雰囲気下で、アドバンテスト社製のR8340抵抗計を用いて、印加電圧500V、印加時間1分の条件で、表面固有抵抗値(Ω/□)を測定した。測定は5点について行い、その平均値を求めた。
得られた表面固有抵抗値測定用試験片(100mm×100mm×3mm)の表面を流水中ウエスで50回拭いた後、25℃、湿度60%に調整された恒温恒湿槽内に24時間静置し、その後、アドバンテスト社製、R8340抵抗計を用いて、印加電圧500V、印加時間1分の条件で、表面固有抵抗値(Ω/□)を測定した。測定は5点で行い、その平均値を求めた。
得られた耐候試験用試験片(60mm×30mm×2mm)を、キセノンウエザオメーター(アトラス社製Ci4000)を用いて、ブラックパネル温度65℃、相対湿度50%、雨スプレーありの条件で試験を実施した。試験開始から3,000時間後の試験片について表面光沢保持率(%)とクラック発生の有無を確認した。なお試験結果について、クラックの発生が認められないものを○、認められたものを×と表記する。
東京電色(株)製グロスメータ、モデルTC−108Dを用いて、測定角度60度における各試験片の光沢を測定した後、上記の耐侯試験を行い、耐侯試験後の試験片の光沢を測定した。この耐侯試験前の光沢に対する耐侯試験後の光沢の100分率を光沢保持率とした。
Claims (11)
- 熱可塑性樹脂60〜98質量部に対し、高分子化合物(A)2〜40質量部であり、前記熱可塑性樹脂と前記高分子化合物の合計量100質量部に対して、ヒンダードアミン化合物(B)0.001〜5質量部および紫外線吸収剤(H)0.001〜10質量部を含有する帯電防止性熱可塑性樹脂組成物において、
前記高分子化合物(A)が、ジオール、脂肪族ジカルボン酸、および芳香族ジカルボン酸から構成されるポリエステル(E)と、下記一般式(1)、
で表される基を一つ以上有し、両末端に水酸基を有する化合物(C)と、反応性官能基を有する化合物(D)とが、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有することを特徴とする帯電防止性熱可塑性樹脂組成物。 - 前記ヒンダードアミン化合物(B)が、下記一般式(2)、(4)、(5)、(6)および(7)、
(式(2)中、R1は水素原子、ヒドロキシ基、炭素原子数1〜30の直鎖または分岐を有するアルキル基、ヒドロキシアルキル基、アルコキシ基、ヒドロキシアルコキシ基またはオキシラジカルを表し、R2は、直鎖または分岐を有する炭素原子数1〜31の脂肪族炭化水素基、または、下記一般式(3)で表される置換基を表し、nは1〜4の整数を表すが、R2が一般式(3)で表される置換基である場合、nは1を表す。)
(式(3)中、R1は、式(2)と同じものを表す。)
(式(4)中、R1は、式(2)と同じものを表す。)
(式(5)中、R1は、式(2)と同じものを表し、Yは、直接結合またはメチレン基を表し、rは1〜20の整数を表す。)
(式(6)中、R1は、式(2)と同じものを表し、R3は、直鎖または分岐を有する炭素原子数1〜31のアルキル基、直鎖または分岐を有する炭素原子数2〜31のアルケニル基、2,2,6,6−テトラメチルピペリジル基、または、1,2,2,6,6−ペンタメチルピペリジル基を表し、sは2〜20の整数を表す。)
(式(7)中、uは、2〜20の数を表す。)で表される化合物からなる群から選ばれる少なくとも一種である請求項1記載の帯電防止性熱可塑性樹脂組成物。 - 前記紫外線吸収剤(H)が、下記一般式(8)〜(12)、
(式(8)中のR4およびR5は、各々独立して、水素原子、塩素原子、または、直鎖または分岐を有する炭素原子数1〜4のアルキル基を表し、R6およびR7は、各々独立して、水素原子、または、直鎖または分岐を有する炭素原子数1〜18のアルキル基、炭素原子数1〜18のヒドロキシアルキル基、炭素原子数1〜18のアルコキシ基、炭素原子数1〜18のヒドロキシアルコキシ基、炭素原子数7〜30のアルキルアリール基を表し、R8、R9は各々独立に、水素原子、または、直鎖または分岐を有する炭素原子数1〜4のアルキル基を表す。)、
(式(9)中のR10は、式(8)のR4と同じものを表し、R12、R13は各々独立に、水素原子、直鎖または分岐を有する炭素原子数1〜18のアルキル基、炭素原子数1〜18のヒドロキシアルキル基、炭素原子数1〜18のアルコキシ基、炭素原子数1〜18のヒドロキシアルコキシ基、炭素原子数7〜30のアルキルアリール基、炭素原子数7〜30のアリールアルキル基、炭素原子数3〜20のアルケニル基、および炭素原子数9〜20のN−アルキレンシクロヘキセン−1,2−ジカルボイミド基を表し、kは1または2を表し、kが1の場合、R11は、水素原子、直鎖または分岐を有する炭素原子数1〜18のアルキル基、炭素原子数1〜18のヒドロキシアルキル基、炭素原子数1〜18のアルコキシ基、炭素原子数1〜18のヒドロキシアルコキシ基、炭素原子数7〜30のアルキルアリール基、炭素原子数7〜30のアリールアルキル基、炭素原子数3〜20のアルケニル基、および炭素原子数9〜20のN−アルキレンシクロヘキセン−1,2−ジカルボイミド基を表し、kが2の場合、R11は、炭素原子数1〜20のアルカンジイル基を表し、R11、R12およびR13のアルキル基、ヒドロキシアルキル基、アルコキシ基、ヒドロキシアルコキシ基、アルキルアリール基、アリールアルキル基、アルケニル基およびアルカンジイル基中のメチレン基が、エチレングリコール、プロピレングリコール、−O−、−CO−、−OCO−、−COO−で置換されていてもよい。)
(式(10)中のR14は、直鎖または分岐を有する炭素原子数1〜20のアルキル基、炭素原子数3〜8のシクロアルキル基、炭素原子数3〜20のアルケニル基、炭素原子数6〜20のアリール基、炭素原子数7〜30のアルキルアリール基または炭素原子数7〜30のアリールアルキル基を表し、R15は水素原子、直鎖または分岐を有する炭素原子数1〜8のアルキル基または炭素原子数3〜8のアルケニル基を表し、R16は水素原子、ヒドロキシ基、炭素原子数1〜8のアルキル基、または、−O−R14を表し、R17は水素原子、炭素原子数1〜8のアルキル基、−O−R14または炭素原子6〜20のアリール基を表し、R14〜R17のアルキル基、アルケニル基、アルキルアリール基、アリールアルキル基中のメチレン基およびシクロアルキル基の環状構造を形成する炭素原子が、−O−、−S−、−CO−、−O−CO−、−CO−O−、-NR’−で置き換わっていてもよく、アルキル基、シクロアルキル基、アルケニル基、アリール基、アルキルアリール基およびアリールアルキル基の水素原子が、ヒドロキシ基、ハロゲン原子、炭素原子数1〜12のアルキル基、または炭素原子数1〜12のアルコキシ基で置換されていてもよく、R’は、水素原子または炭素原子数1〜18のアルキル基を表し、複数のR14,R15,R16およびR17は、各々、同一であってもよく、異なるものであってもよい)
(式(11)中のR18は、水素原子、ヒドロキシ基、直鎖または分岐を有する炭素原子数1〜8のアルキル基を表わし、複数のR18は、各々異なるものであってもよく、同一であってもよい。wは4〜14の数を表す。)
(式(12)中のR19、R20およびR21は各々独立に、水素原子、塩素原子、ヒドロキシ基、カルボキシル基、直鎖または分岐を有する炭素原子数1〜18のアルキル基、炭素原子数1〜18のヒドロキシアルキル基、炭素原子数1〜18のアルコキシ基、炭素原子数1〜18のヒドロキシアルコキシ基、炭素原子数7〜30のアルキルアリール基、炭素原子数7〜30のアルコキシアリール基、アセトフェノン、炭素原子数4〜15のアクリロイルオキシアルコキシ基または炭素原子数5〜15のメタクリロイルオキシアルコキシ基、ヒドロキシベンゾフェノキシアルキルオキシ基を表し、R22、R23は各々独立に、水素原子、塩素原子、ヒドロキシ基、スルホニル基、ナトリウムスルホニル基、ヒドロキシスルホニル基、アクリロイルオキシアルコキシ基を表す。)で表される化合物からなる群のうち1種以上である請求項1または2記載の帯電防止性熱可塑性樹脂組成物。 - 前記高分子化合物(A)が、前記ポリエステル(E)から構成されたブロックおよび前記化合物(C)から構成されたブロックがエステル結合を介して繰り返し交互に結合してなる両末端にカルボキシル基を有するブロックポリマー(G)と、前記化合物(D)とが、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有する請求項1〜3のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- 前記ポリエステル(E)から構成されたブロックの数平均分子量がポリスチレン換算で800〜8,000であり、前記化合物(C)から構成されたブロックの数平均分子量がポリスチレン換算で400〜6,000であり、かつ、前記ブロックポリマー(G)の数平均分子量が、ポリスチレン換算で、5,000〜25,000である請求項4記載の帯電防止性熱可塑性樹脂組成物。
- 前記ポリエステル(E)が、両末端にカルボキシル基を有する構造である請求項1〜5のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- 前記化合物(D)が、2個以上のエポキシ基を有する多価エポキシ化合物(D)−1、3個以上の水酸基を有する多価アルコール化合物(D)−2、および2個以上のアミノ基を有する多価アミン化合物(D)−3からなる群から選ばれる少なくとも一種である請求項1〜6のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- 前記化合物(C)が、ポリエチレングリコールである請求項1〜7のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- さらに、1種以上のアルカリ金属塩(F)0.01〜5質量部を含有する請求項1〜8のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- 前記熱可塑性樹脂が、ポリオレフィン系樹脂、スチレン系樹脂、ポリエステル系樹脂、ポリエーテル系樹脂、ポリカーボネート系樹脂、ポリアミド系樹脂、および含ハロゲン樹脂からなる群から選ばれる少なくとも一種である請求項1〜9のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- 請求項1〜10のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物が成形されてなることを特徴とする成形体。
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