JPWO2016084954A1 - 熱可塑性樹脂用帯電防止剤および熱可塑性樹脂組成物 - Google Patents
熱可塑性樹脂用帯電防止剤および熱可塑性樹脂組成物 Download PDFInfo
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- JPWO2016084954A1 JPWO2016084954A1 JP2016513930A JP2016513930A JPWO2016084954A1 JP WO2016084954 A1 JPWO2016084954 A1 JP WO2016084954A1 JP 2016513930 A JP2016513930 A JP 2016513930A JP 2016513930 A JP2016513930 A JP 2016513930A JP WO2016084954 A1 JPWO2016084954 A1 JP WO2016084954A1
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- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- QCIWPAJGVAANGJ-UHFFFAOYSA-N tribromomethoxybenzene Chemical compound BrC(Br)(Br)OC1=CC=CC=C1 QCIWPAJGVAANGJ-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- BZEKAGQVXIXMFJ-UHFFFAOYSA-N trifluoromethanesulfonic acid 1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound OS(C(F)(F)F)(=O)=O.O=S(C(F)(F)F)(NS(C(F)(F)F)(=O)=O)=O BZEKAGQVXIXMFJ-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- ACZOGADOAZWANS-UHFFFAOYSA-N trimethyl(pentyl)azanium Chemical compound CCCCC[N+](C)(C)C ACZOGADOAZWANS-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
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
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- C08L101/00—Compositions of unspecified macromolecular compounds
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- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
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- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Aは炭素数2〜4の直鎖状または分枝状のアルキレン基であり、
nは0〜50の整数であり、
Q1+は、第2級アンモニウムイオンまたは第3級アンモニウムイオンである、
Q2+は、第2級アンモニウムイオンまたは第3級アンモニウムイオンである。
本形態に係る熱可塑性樹脂用帯電防止剤において、当該イオン結合性塩は、化学式(1)のものを1種単独で用いてもよいし、2種以上併用してもよいし、化学式(2)のものを1種単独で用いてもよいし、2種以上併用してもよいし、化学式(1)のものの1種または2種以上と、化学式(2)のものの1種または2種以上とを組み合わせて用いてもよい。ただし、化学式(2)で表されるイオン結合性塩を少なくとも1種用いることが好ましい。
本形態に係る熱可塑性樹脂用帯電防止剤において、高分子型帯電防止剤としては、従来公知の高分子型帯電防止剤(高分子構造を有する帯電防止剤)がいずれも好適に用いられうる。ただし、上述した「化学式(1)または化学式(2)で表されるイオン結合性塩」は、高分子構造を有していたとしても本発明における「高分子型帯電防止剤」の概念には含めないものとする。
い。
上記高分子型帯電防止剤は、単独で用いてもよいし、組み合わせて使用してもよい。
本発明の他の形態によれば、熱可塑性樹脂と、上述した形態に係る熱可塑性樹脂用帯電防止剤とを含む、熱可塑性樹脂組成物もまた、提供される。
本実施例では、下記化学式(明細書中の化学式(23))で表されるクメンスルホン酸N−エチルアミノエタノール([MEM][Cum−SO3])を、熱可塑性樹脂用帯電防止剤を構成するイオン結合性塩として準備した。
本実施例では、上記イオン結合性塩以外の帯電防止剤として、以下のものを準備した。〈高分子型帯電防止剤〉
・「IonPhasE(登録商標) IPE(登録商標) U2」(IonPhasE社製)
・「ペレスタット(登録商標)NC6321」(三洋化成工業社製)
・「ペレスタット(登録商標)230」(三洋化成工業社製)
・「ペレクトロン(登録商標)AS」(三洋化成工業社製)
[熱可塑性樹脂組成物の評価例1]
ABS樹脂(PA−758;Chi Mei社製)に、上述した「他の帯電防止剤」のいずれかを、混合後の含有量が2重量%、5重量%または10重量%のいずれかとなるように添加して、ABS樹脂と他の帯電防止剤との混合物を得た。続いて、実施例(本発明の実験例)では、得られた混合物に、上述したイオン結合性塩([MEM][Cum−SO3])を、当該混合物の重量に対する添加量が2重量%となるように添加した。一方、比較例(本発明を外れる実験例)では、上記イオン結合性塩を添加しなかった(添加した帯電防止剤の種類および添加量については、下記の表1〜3を参照)。
ABS樹脂(スタイラック(登録商標)−ABS190F;旭化成ケミカルズ株式会社製)100重量部に、上述した「他の帯電防止剤」(高分子型帯電防止剤)である「ペレスタットNC6321」を、混合後の含有量が10重量%となるように添加して、ABS樹脂と高分子型帯電防止剤との混合物を得た。続いて、実施例(本発明の実験例)では、得られた混合物に、上述したイオン結合性塩([MEM][Cum−SO3])を、当該混合物の重量に対する添加量が2重量%となるように添加した。一方、比較例(本発明を外れる実験例)では、上記イオン結合性塩を添加しなかった(添加した帯電防止剤の種類および添加量については、下記の表4を参照)。
アクリル樹脂(ACRYREX(登録商標);Chi Mei社製)に、上述した「他の帯電防止剤」である「ペレスタット230」を、最終組成物における含有量が10重量%となるように添加して、アクリル樹脂と他の帯電防止剤との混合物を得た。続いて、実施例(本発明の実験例)では、得られた混合物に、上述したイオン結合性塩([MEM][Cum−SO3])を、最終組成物における含有量が2重量%(樹脂と他の帯電防止剤との合計重量に対する添加量として2.04重量%)となるように添加した。一方、比較例(本発明を外れる実験例)では、上記イオン結合性塩を添加せず、アクリル樹脂とペレスタット230との混合比を80:20(重量比)とした。
アクリル樹脂に代えて、ポリプロピレン樹脂であるサンアロマー(登録商標)(サンアロマー株式会社製)を用いたこと以外は、上述した「熱可塑性樹脂組成物の評価例3」と同様にして、比較例9および実施例11を実施した。表面抵抗率の測定結果を下記の表6に示す。
Claims (12)
- 下記化学式(1)または下記化学式(2)で表されるイオン結合性塩と、高分子型帯電防止剤との混合物を含む、熱可塑性樹脂用帯電防止剤:
Aは炭素数2〜4の直鎖状または分枝状のアルキレン基であり、
nは0〜50の整数であり、
Q1+は、第2級アンモニウムイオンまたは第3級アンモニウムイオンである、
Q2+は、第2級アンモニウムイオンまたは第3級アンモニウムイオンである。 - 前記化学式(2)で表されるイオン結合性塩を含む、請求項1に記載の熱可塑性樹脂用帯電防止剤。
- Q1+およびQ2+が第2級アンモニウムイオンである、請求項1または2に記載の熱可塑性樹脂用帯電防止剤。
- Q1+およびQ2+がヒドロキシ基を有するものである、請求項1〜3のいずれか1項に記載の熱可塑性樹脂用帯電防止剤。
- Q1+およびQ2+は、ヒドロキシエチル基が窒素原子に結合した構造を有する、請求項4に記載の熱可塑性樹脂用帯電防止剤。
- 前記イオン結合性塩が、下記化学式(23)〜(26)のいずれかで表されるものである、請求項1〜5のいずれか1項に記載の熱可塑性樹脂用帯電防止剤。
- 前記高分子型帯電防止剤が、親水基を有しブロック共重合されているポリエーテル類からなる、請求項1〜6のいずれか1項に記載の熱可塑性樹脂用帯電防止剤。
- 前記熱可塑性樹脂が、ABS樹脂である、請求項1〜7のいずれか1項に記載の熱可塑性樹脂用帯電防止剤。
- 熱可塑性樹脂と、
請求項1〜7のいずれか1項に記載の熱可塑性樹脂用帯電防止剤と、
を含む、熱可塑性樹脂組成物。 - 前記熱可塑性樹脂が、ABS樹脂である、請求項9に記載の熱可塑性樹脂組成物。
- 下記化学式(1)または下記化学式(2)で表されるイオン結合性塩と、高分子型帯電防止剤との混合物の、熱可塑性樹脂用帯電防止剤としての使用:
Aは炭素数2〜4の直鎖状または分枝状のアルキレン基であり、
nは0〜50の整数であり、
Q1+は、第2級アンモニウムイオンまたは第3級アンモニウムイオンである、
Q2+は、第2級アンモニウムイオンまたは第3級アンモニウムイオンである。 - 下記化学式(1)または下記化学式(2)で表されるイオン結合性塩と、高分子型帯電防止剤との混合物を熱可塑性樹脂へ添加する工程を含む、熱可塑性樹脂の帯電防止性を向上させる方法:
Aは炭素数2〜4の直鎖状または分枝状のアルキレン基であり、
nは0〜50の整数であり、
Q1+は、第2級アンモニウムイオンまたは第3級アンモニウムイオンである、
Q2+は、第2級アンモニウムイオンまたは第3級アンモニウムイオンである。
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