JP5762437B2 - 帯電防止熱可塑性組成物 - Google Patents
帯電防止熱可塑性組成物 Download PDFInfo
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- JP5762437B2 JP5762437B2 JP2012542491A JP2012542491A JP5762437B2 JP 5762437 B2 JP5762437 B2 JP 5762437B2 JP 2012542491 A JP2012542491 A JP 2012542491A JP 2012542491 A JP2012542491 A JP 2012542491A JP 5762437 B2 JP5762437 B2 JP 5762437B2
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- Prior art keywords
- butyl
- ethyl
- methylimidazolium
- tert
- group
- Prior art date
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- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 1
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- NTTIENRNNNJCHQ-UHFFFAOYSA-N octyl n-(3,5-ditert-butyl-4-hydroxyphenyl)carbamate Chemical compound CCCCCCCCOC(=O)NC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NTTIENRNNNJCHQ-UHFFFAOYSA-N 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
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- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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- 150000002978 peroxides Chemical class 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
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- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-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
- 229920006344 thermoplastic copolyester Polymers 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- UVZICZIVKIMRNE-UHFFFAOYSA-N thiodiacetic acid Chemical compound OC(=O)CSCC(O)=O UVZICZIVKIMRNE-UHFFFAOYSA-N 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 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
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
-
- A—HUMAN NECESSITIES
- A43—FOOTWEAR
- A43B—CHARACTERISTIC FEATURES OF FOOTWEAR; PARTS OF FOOTWEAR
- A43B7/00—Footwear with health or hygienic arrangements
- A43B7/36—Footwear with health or hygienic arrangements with earthing or grounding means
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0075—Antistatics
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3415—Five-membered rings
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
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Description
本発明は、極性熱可塑性ポリマー及びイオン液体を含む帯電防止組成物の、非極性熱可塑性ポリマー又は弾性ポリマーのための帯電防止添加剤としての使用に関する。本発明の更なる態様は、極性熱可塑性ポリマーとイオン液体との混合物並びに極性熱可塑性ポリマー、イオン液体及び非極性熱可塑性又は弾性ポリマーの組成物をそこに導入することを含む、帯電防止非極性熱可塑性又は弾性ポリマーの製造方法である。
a)極性熱可塑性ポリマー;及び
b)有機イオン液体
を含み、該液体は
カチオンとして、
メチルトリ−(1−ブチル)アンモニウム、2−ヒドロキシエチルアンモニウム、1−メチルイミダゾリウム、1−エチルイミダゾリウム、1−(1−ブチル)イミダゾリウム、1−(1−オクチル)イミダゾリウム、1−(1−ドデシル)イミダゾリウム、1−(1−テトラデシル)イミダゾリウム、1−(1−ヘキサデシル)イミダゾリウム、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、1−(1−ブチル)−3−メチルイミダゾリウム、1−(1−ブチル)−3−エチルイミダゾリウム、1−(1−ヘキシル)−3−メチルイミダゾリウム、1−(1−ヘキシル)−3−エチルイミダゾリウム、1−(1−ヘキシル)−3−ブチルイミダゾリウム、1−(1−オクチル)−3−メチルイミダゾリウム、1−(1−オクチル)−3−エチルイミダゾリウム、1−(1−オクチル)−3−ブチルイミダゾリウム、1−(1−ドデシル)−3−メチルイミダゾリウム、1−(1−ドデシル)−3−エチルイミダゾリウム、1−(1−ドデシル)−3−ブチルイミダゾリウム、1−(1−ドデシル)−3−オクチルイミダゾリウム、1−(1−テトラデシル)−3−メチルイミダゾリウム、1−(1−テトラデシル)−3−エチルイミダゾリウム、1−(1−テトラデシル)−3−ブチルイミダゾリウム、1−(1−テトラデシル)−3−オクチルイミダゾリウム、1−(1−ヘキサデシル)−3−メチル−イミダゾリウム、1−(1−ヘキサデシル)−3−エチルイミダゾリウム、1−(1−ヘキサデシル)−3−ブチル−イミダゾリウム、1−(1−ヘキサデシル)−3−オクチルイミダゾリウム、1,2−ジメチルイミダゾリウム、1,2,3−トリメチルイミダゾリウム、1−エチル−2,3−ジメチルイミダゾリウム、1−(1−ブチル)−2,3−ジメチル−イミダゾリウム、1−(1−ヘキシル)−2,3−ジメチル−イミダゾリウム、1−(1−オクチル)−2,3−ジメチル−イミダゾリウム、1,4−ジメチルイミダゾリウム、1,3,4−トリメチルイミダゾリウム、1,4−ジメチル−3−エチルイミダゾリウム、3−ブチルイミダゾリウム、1,4−ジメチル−3−オクチルイミダゾリウム、1,4,5−トリメチルイミダゾリウム、1,3,4,5−テトラメチルイミダゾリウム、1,4,5−トリメチル−3−エチルイミダゾリウム、1,4,5−トリメチル−3−ブチルイミダゾリウム又は1,4,5−トリメチル−3−オクチルイミダゾリウム、並びに
アニオンとして
クロリド、ブロミド、硫化水素、テトラクロロアルミネート、チオシアネート、メチルスルフェート、エチルスルフェート、メタンスルホネート、ホルメート、アセテート、ジメチルホスフェート、ジエチルホスフェート、p−トルエンスルホネート、テトラフルオロボレート又はヘキサフルオロホスフェートからなる群から選択される、組成物の、非極性熱可塑性又は弾性ポリマーのための帯電防止剤としての使用である。
メチルトリ−(1−ブチル)アンモニウム、2−ヒドロキシエチルアンモニウム、1−メチルイミダゾリウム、1−エチルイミダゾリウム、1−(1−ブチル)イミダゾリウム、1−(1−オクチル)イミダゾリウム、1−(1−ドデシル)イミダゾリウム、1−(1−テトラデシル)イミダゾリウム、1−(1−ヘキサデシル)イミダゾリウム、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、1−(1−ブチル)−3−メチルイミダゾリウム、1−(1−ブチル)−3−エチルイミダゾリウム、1−(1−ヘキシル)−3−メチルイミダゾリウム、1−(1−ヘキシル)−3−エチル−イミダゾリウム、1−(1−ヘキシル)−3−ブチルイミダゾリウム、1−(1−オクチル)−3−メチルイミダゾリウム、1−(1−オクチル)−3−エチルイミダゾリウム、1−(1−オクチル)−3−ブチルイミダゾリウム、1−(1−ドデシル)−3−メチルイミダゾリウム、1−(1−ドデシル)−3−エチルイミダゾリウム、1−(1−ドデシル)−3−ブチルイミダゾリウム、1−(1−ドデシル)−3−オクチルイミダゾリウム、1−(1−テトラデシル)−3−メチルイミダゾリウム、1−(1−テトラデシル)−3−エチルイミダゾリウム、1−(1−テトラデシル)−3−ブチルイミダゾリウム、1−(1−テトラデシル)−3−オクチルイミダゾリウム、1−(1−ヘキサデシル)−3−メチルイミダゾリウム、1−(1−ヘキサデシル)−3−エチルイミダゾリウム、1−(1−ヘキサデシル)−3−ブチルイミダゾリウム、1−(1−ヘキサデシル)−3−オクチルイミダゾリウム、1,2−ジメチルイミダゾリウム、1,2,3−トリメチルイミダゾリウム、1−エチル−2,3−ジ−メチルイミダゾリウム、1−(1−ブチル)−2,3−ジメチルイミダゾリウム、1−(1−ヘキシル)−2,3−ジメチル−イミダゾリウム、1−(1−オクチル)−2,3−ジメチルイミダゾリウム、1,4−ジメチルイミダゾリウム、1,3,4−トリ−メチルイミダゾリウム、1,4−ジメチル−3−エチルイミダゾリウム、3−ブチルイミダゾリウム、1,4−ジメチル−3−オクチルイミダゾリウム、1,4,5−トリメチルイミダゾリウム、1,3,4,5−テトラメチルイミダゾリウム、1,4,5−トリメチル−3−エチルイミダゾリウム、1,4,5−トリメチル−3−ブチルイミダゾリウム又は1,4,5−トリメチル−3−オクチルイミダゾリウム;並びに
アニオンとして、
クロリド、ブロミド、ハイドロゲンサルフェート、テトラクロロアルミネート、チオシアネート、メチルスルフェート、エチルスルフェート、メタンスルホネート、ホルメート、アセテート、ジメチルホスフェート、ジエチルホスフェート、p−トルエンスルホネート、テトラフルオロボレート又はヘキサフルオロホスフェートからなる群から選択される。
a)ラジカルに(通常、高圧及び高温にて)
b)触媒、通常、1つ以上の第IVb族、第Vb族、第VIb族又は第VIII族の金属を含有する触媒によって、製造できる。それらの金属は通常、1つ以上の配位子、例えば、オキシド、ハライド、アルコレート、エステル、エーテル、アミン、アルキル、アルケニル及び/又はアリールを有し、それらはπ又はσ配位のいずれであってもよい。それらの金属錯体は、遊離しているか又は担体に、例えば、活性化塩化マグネシウム、塩化チタン(III)、酸化アルミニウム又は酸化ケイ素に固定されていてよい。それらの触媒は重合媒体中で可溶性又は不溶性であってよい。触媒自体を重合において活性化できるか又は更なる活性剤、例えば、金属アルキル、金属水素化物、金属アルキルハライド、金属アルキルオキシド又は金属アルキルオキサンを使用してよく、該金属は第Ia族、第IIa族及び/又は第IIIa族の元素である。活性剤は、更なるエステル、エーテル、アミン又はシリルエーテル基で変性してよい。それらの触媒系は通常、Phillips、Standard Oil Indiana、Ziegler(−Natta)、TNZ(DuPont)、メタロセン又はシングルサイト触媒(SSC)として知られている。
1. アルキル化モノフェノール、例えば、2,6−ジ−tert−ブチル−4−メチルフェノール、2−ブチル−4,6−ジメチルフェノール、2,6−ジ−tert−ブチル−4−エチルフェノール、2,6−ジ−tert−ブチル−4−n−ブチルフェノール、2,6−ジ−tert−ブチル−4−イソブチルフェノール、2,6−ジシクロペンチル−4−メチルフェノール、2−(α−メチルシクロヘキシル)−4,6−ジメチルフェノール、2,6−ジオクタデシル−4−メチルフェノール、2,4,6−トリシクロヘキシルフェノール、2,6−ジ−tert−ブチル−4−メトキシメチルフェノール、2,6−ジ−ノニル−4−メチルフェノール、2,4−ジメチル−6−(1’−メチルウンデカ−1’−イル)−フェノール、2,4−ジメチル−6−(1’−メチル−ヘプタデカ−1’−イル)フェノール、2,4−ジメチル−6−(1’−メチル−トリデカ−1’−イル)フェノール、オクチルフェノール、ノニルフェノール及びそれらの混合物。
好ましいものは、群5、10及び14の酸化防止剤、特に2,2−ビス(4−ヒドロキシフェニル)−プロパン、3,5−ジ−tert−ブチル−4−ヒドロキシフェニルプロピオン酸とオクタデカノール又はペンタエリトリトールとのエステル又はトリス−(2,4−ジ−tert−ブチルフェニル)−ホスフィットである。
1. 2−(2’−ヒドロキシフェニル)ベンゾトリアゾール、例えば、2−(2’−ヒドロキシ−5’−メチルフェニル)−ベンゾトリアゾール、2−(3’,5’−ジ−tert−ブチル−2’−ヒドロキシフェニル)−ベンゾトリアゾール、2−(5’−tert−ブチル−2’−ヒドロキシフェニル)−ベンゾトリアゾール、2−(2’−ヒドロキシ−5’−(1,1,3,3−テトラメチルブチル)フェニル)ベンゾトリアゾール、2−(3’,5’−ジ−tert−ブチル−2’−ヒドロキシフェニル)−5−クロロ−ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−メチルフェニル)−5−クロロベンゾトリアゾール、2−(3’−sec−ブチル−5’−tert−ブチル−2’−ヒドロキシフェニル)−ベンゾトリアゾール、2−(2’−ヒドロキシ−4’−オクチルオキシフェニル)−ベンゾトリアゾール、2−(3’,5’−ジ−tert−アミル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’,5’−ビス(α,α−ジメチルベンジル)−2’−ヒドロキシフェニル)ベンゾトリアゾール;2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−オクチルオキシカルボニルエチル)フェニル)−5−クロロベンゾトリアゾール、2−(3’−tert−ブチル−5’−[2−(2−エチルヘキシルオキシ)−カルボニルエチル]−2’−ヒドロキシフェニル)−5−クロロベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−メトキシカルボニルエチル)フェニル)−5−クロロベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−メトキシカルボニルエチル)フェニル)ベンゾトリアゾール、2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−オクチルオキシカルボニルエチル)フェニル)ベンゾトリアゾール、2−(3’−tert−ブチル−5’−[2−(2−エチルヘキシルオキシ)カルボニルエチル]−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’−ドデシル−2’−ヒドロキシ−5’−メチルフェニル)ベンゾトリアゾール、及び2−(3’−tert−ブチル−2’−ヒドロキシ−5’−(2−イソオクチルオキシカルボニルエチル)フェニルベンゾトリアゾールの混合物、2,2’−メチレン−ビス[4−(1,1,3,3−テトラメチルブチル)−6−ベンゾトリアゾール−2−イルフェノール];2−[3’−tert−ブチル−5’−(2−メトキシカルボニルエチル)−2−ヒドロキシフェニル]−ベンゾトリアゾールとポリエチレングリコール300とのエステル交換反応生成物;[R−CH2CH2−COO(CH2)3]−(式中、R=3’−tert−ブチル−4’−ヒドロキシ−5’−2H−ベンゾトリアゾール−2−イル−フェニル)。
a)極性熱可塑性ポリマー;及び
b)有機イオン液体
の混合物を導入することを含み、その際、該イオン液体が、
カチオンとして
メチルトリ−(1−ブチル)アンモニウム、2−ヒドロキシエチルアンモニウム、1−メチルイミダゾリウム、1−エチルイミダゾリウム、1−(1−ブチル)イミダゾリウム、1−(1−オクチル)イミダゾリウム、1−(1−ドデシル)イミダゾリウム、1−(1−テトラデシル)イミダゾリウム、1−(1−ヘキサデシル)イミダゾリウム、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、1−(1−ブチル)−3−メチルイミダゾリウム、1−(1−ブチル)−3−エチルイミダゾリウム、1−(1−ヘキシル)−3−メチルイミダゾリウム、1−(1−ヘキシル)−3−エチルイミダゾリウム、1−(1−ヘキシル)−3−ブチルイミダゾリウム、1−(1−オクチル)−3−メチルイミダゾリウム、1−(1−オクチル)−3−エチルイミダゾリウム、1−(1−オクチル)−3−ブチルイミダゾリウム、1−(1−ドデシル)−3−メチルイミダゾリウム、1−(1−ドデシル)−3−エチルイミダゾリウム、1−(1−ドデシル)−3−ブチルイミダゾリウム、1−(1−ドデシル)−3−オクチルイミダゾリウム、1−(1−テトラデシル)−3−メチルイミダゾリウム、1−(1−テトラデシル)−3−エチルイミダゾリウム、1−(1−テトラデシル)−3−ブチルイミダゾリウム、1−(1−テトラデシル)−3−オクチルイミダゾリウム、1−(1−ヘキサデシル)−3−メチルイミダゾリウム、1−(1−ヘキサデシル)−3−エチルイミダゾリウム、1−(1−ヘキサデシル)−3−ブチルイミダゾリウム、1−(1−ヘキサデシル)−3−オクチルイミダゾリウム、1,2−ジメチルイミダゾリウム、1,2,3−トリメチルイミダゾリウム、1−エチル−2,3−ジメチルイミダゾリウム、1−(1−ブチル)−2,3−ジメチルイミダゾリウム、1−(1−ヘキシル)−2,3−ジメチル−イミダゾリウム、1−(1−オクチル)−2,3−ジメチルイミダゾリウム、1,4−ジメチルイミダゾリウム、1,3,4−トリメチルイミダゾリウム、1,4−ジメチル−3−エチルイミダゾリウム、3−ブチルイミダゾリウム、1,4−ジメチル−3−オクチルイミダゾリウム、1,4,5−トリメチルイミダゾリウム、1,3,4,5−テトラメチルイミダゾリウム、1,4,5−トリメチル−3−エチルイミダゾリウム、1,4,5−トリメチル−3−ブチルイミダゾリウム又は1,4,5−トリメチル−3−オクチルイミダゾリウム;並びに
アニオンとして、
クロリド、ブロミド、ハイドロゲンサルフェート、テトラクロロアルミネート、チオシアネート、メチルスルフェート、エチルスルフェート、メタンスルホネート、ホルメート、アセテート、ジメチルホスフェート、ジエチルホスフェート、p−トルエンスルホネート、テトラフルオロボレート又はヘキサフルオロホスフェートからなる群から選択される、
前記製造方法である。
a)極性熱可塑性ポリマー;及び
b)有機イオン液体
の混合物を含み、その際、該イオン液体が、
カチオンとして
メチルトリ−(1−ブチル)アンモニウム、2−ヒドロキシエチルアンモニウム、1−メチルイミダゾリウム、1−エチルイミダゾリウム、1−(1−ブチル)イミダゾリウム、1−(1−オクチル)イミダゾリウム、1−(1−ドデシル)イミダゾリウム、1−(1−テトラデシル)イミダゾリウム、1−(1−ヘキサデシル)イミダゾリウム、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、1−(1−ブチル)−3−メチルイミダゾリウム、1−(1−ブチル)−3−エチルイミダゾリウム、1−(1−ヘキシル)−3−メチルイミダゾリウム、1−(1−ヘキシル)−3−エチルイミダゾリウム、1−(1−ヘキシル)−3−ブチルイミダゾリウム、1−(1−オクチル)−3−メチルイミダゾリウム、1−(1−オクチル)−3−エチルイミダゾリウム、1−(1−オクチル)−3−ブチルイミダゾリウム、1−(1−ドデシル)−3−メチルイミダゾリウム、1−(1−ドデシル)−3−エチルイミダゾリウム、1−(1−ドデシル)−3−ブチルイミダゾリウム、1−(1−ドデシル)−3−オクチルイミダゾリウム、1−(1−テトラデシル)−3−メチルイミダゾリウム、1−(1−テトラデシル)−3−エチルイミダゾリウム、1−(1−テトラデシル)−3−ブチルイミダゾリウム、1−(1−テトラデシル)−3−オクチルイミダゾリウム、1−(1−ヘキサデシル)−3−メチルイミダゾリウム、1−(1−ヘキサデシル)−3−エチルイミダゾリウム、1−(1−ヘキサデシル)−3−ブチルイミダゾリウム、1−(1−ヘキサデシル)−3−オクチルイミダゾリウム、1,2−ジメチルイミダゾリウム、1,2,3−トリメチルイミダゾリウム、1−エチル−2,3−ジメチルイミダゾリウム、1−(1−ブチル)−2,3−ジメチルイミダゾリウム、1−(1−ヘキシル)−2,3−ジメチル−イミダゾリウム、1−(1−オクチル)−2,3−ジメチルイミダゾリウム、1,4−ジメチルイミダゾリウム、1,3,4−トリメチルイミダゾリウム、1,4−ジメチル−3−エチルイミダゾリウム、3−ブチルイミダゾリウム、1,4−ジメチル−3−オクチルイミダゾリウム、1,4,5−トリメチルイミダゾリウム、1,3,4,5−テトラメチルイミダゾリウム、1,4,5−トリメチル−3−エチルイミダゾリウム、1,4,5−トリメチル−3−ブチルイミダゾリウム又は1,4,5−トリメチル−3−オクチルイミダゾリウム;並びに
アニオンとして、
クロリド、ブロミド、ハイドロゲンサルフェート、テトラクロロアルミネート、チオシアネート、メチルスルフェート、エチルスルフェート、メタンスルホネート、ホルメート、アセテート、ジメチルホスフェート、ジエチルホスフェート、p−トルエンスルホネート、テトラフルオロボレート又はヘキサフルオロホスフェートからなる群から選択される組成物であって、非極性熱可塑性又は弾性ポリマー中に導入される前記組成物である。
使用する材料
PP:ポリプロピレンホモポリマー、Borealis社製のMFR4(230℃/2.16kg)
IPS:高耐衝撃性ポリスチレン、Styron LLC社製のMFR10(200℃/5kg)
IL1:イオン液体1、BASF SE社製の1−エチル−3−メチルイミダゾリウム−エチルサルフェート(EMIM−ES)
PO:極性熱可塑性ポリマー、ポリマーマトリックスでのイオン液体(IL)のための相容化樹脂
PO1:ポリエーテルエステルアミド、BASF SE社製のIrgastat(登録商標)P16
PO2:極めて吸湿性のアイオノマー樹脂をベースとしたエチレンコポリマー、DuPont社製のEntira AS MK 400
PO3:熱可塑性ポリウレタンエラストマー(ポリエーテル)、BASF SE社製のElastollane 1190 A 10
PO4:熱可塑性ポリウレタンエラストマー、Bayer Material Science社製のDesmopan DP 6580 A MVT
PO5:熱可塑性コポリエステルエラストマー、DSM Engineering Plastics社製のArnitel VT 3108
方法A
396gのPO1(ペレット)を丸底フラスコ中に入れる。4gのIL1を加える。混合物を55℃で4時間回転させた後、IL1にPOが完全に浸漬する。混合物を90℃で16時間、真空下で乾燥させる。
396gのPO(ペレット)をそれぞれ丸底フラスコ中に入れる。20gの水に溶解した4gのIL1を添加する。混合物を55℃で3時間回転させた後、IL1溶液にPOが完全に浸漬する。混合物を90℃で16時間、真空下で乾燥させる。
実施例
PP又はIPSペレットを、方法Bに記載される通りに調製された、異なる濃度の導電ペレットと乾燥ブレンドする(表1による組成物)。混合物を230℃で2mm厚さのプラークで射出成形する。プラークの表面抵抗率を決定する。組成物及び得られた表面抵抗率を、同様に調製された比較例CE−1〜CE−12と一緒に表2に示す。
使用する極性熱可塑性ポリマーを以下に示す:
A1:150ml/gの粘度数(VN)を示すポリアミド6。
試験するイオン液体を以下に列記する:
− B1:1−エチル−3−メチルイミダゾリウムトリフルイミド(CAS#174899−82−2)
− B2:1−エチル−3−メチルイミダゾリウムエチルスルフェート(CAS#342573−75−5)
− B3:1−エチル−3−メチルイミダゾリウムテトラフルオロボレート(CAS#143314−16−3)
− B4:1−エチル−3−メチルイミダゾリウムトリフラート(CAS#145022−44−2)
ポリアミドの粘度数を、25℃にて96質量%の硫酸中の0.5質量%の溶液としてISO307に従って測定する。
電源:Keithley Instruments, 225 Current Source
電圧測定:Keithley Instruments, 617 Programmable Electrometer
電流測定:Keithley Instruments, 1000 Multimeter。
試料を、Coperion社製の共回転二軸スクリュー押出機−ZSK18、即ち、様々な処理領域を有するスクリュー直径18mmのものを用いて調製する。供給領域、溶融領域、運搬領域、排気領域、分散領域等がある。
Claims (6)
- a)アイオノマー、ポリエチレングリコール変性ポリエチレンテレフタレート、ポリアミド、コポリエステルエラストマー、ポリエーテルエステルアミド及び熱可塑性ポリウレタンからなる群から選択されるポリマー;及び
b)メチルイミダゾリウムクロリド、1−エチル−3−メチルイミダゾリウムエチルスルフェート、1−ブチル−3−メチル−イミダゾリウムメチルスルフェート、1−エチル−3−メチルイミダゾリウムメタンスルホネート、1−エチル−2,3−ジメチルイミダゾリウムエチルスルフェート、1−ブチル−3−メチルイミダゾリウムクロリド、1−ブチル−3−メチルイミダゾリウムメタンスルホネート、1−エチル−3−メチルイミダゾリウムクロリド、1−エチル−3−メチルイミダゾリウムチオシアネート及び1−ブチル−3−メチルイミダゾリウムチオシアネートからなる群から選択される有機イオン液体であって、大気圧(1バール)で180℃未満の融点を有する塩である有機イオン液体
を含む組成物の、
ポリエチレン及びそのコポリマー、ポリプロピレン及びそのコポリマー並びにスチレン及びそのコポリマーからなる群から選択される熱可塑性ポリマーのための帯電防止添加剤としての使用。 - 成分b)の量が、成分a)の質量を基準として、0.1〜5質量%である、請求項1記載の使用。
- 組成物、成分a)とb)との混合物が、熱可塑性ポリマーの質量を基準として、2〜30質量%の量で存在する、請求項1または2に記載の使用。
- 光安定剤、熱安定剤、処理安定剤、顔料、充填剤、及び清澄剤からなる群から選択される更なる添加剤が存在する、請求項1から3までのいずれか1項に記載の使用。
- ポリエチレン及びそのコポリマー、ポリプロピレン及びそのコポリマー並びにスチレン及びそのコポリマーからなる群から選択される熱可塑性ポリマーの製造方法において、該熱可塑性ポリマー中に、
a)アイオノマー、ポリエチレングリコール変性ポリエチレンテレフタレート、ポリアミド、コポリエステルエラストマー、ポリエーテルエステルアミド、及び熱可塑性ポリウレタンからなる群から選択されるポリマー;及び
b)メチルイミダゾリウムクロリド、1−エチル−3−メチルイミダゾリウムエチルスルフェート、1−ブチル−3−メチル−イミダゾリウムメチルスルフェート、1−エチル−3−メチルイミダゾリウムメタンスルホネート、1−エチル−2,3−ジメチルイミダゾリウムエチルスルフェート、1−ブチル−3−メチルイミダゾリウムクロリド、1−ブチル−3−メチルイミダゾリウムメタンスルホネート、1−エチル−3−メチルイミダゾリウムクロリド、1−エチル−3−メチルイミダゾリウムチオシアネート及び1−ブチル−3−メチルイミダゾリウムチオシアネートからなる群から選択される有機イオン液体であって、大気圧(1バール)で180℃未満の融点を有する塩である有機イオン液体の混合物を導入することを含む、前記製造方法。 - a)アイオノマー、ポリエチレングリコール変性ポリエチレンテレフタレート、ポリアミド、コポリエステルエラストマー、ポリエーテルエステルアミド、及び熱可塑性ポリウレタンからなる群から選択されるポリマー;及び
b)メチルイミダゾリウムクロリド、1−エチル−3−メチルイミダゾリウムエチルスルフェート、1−ブチル−3−メチル−イミダゾリウムメチルスルフェート、1−エチル−3−メチルイミダゾリウムメタンスルホネート、1−エチル−2,3−ジメチルイミダゾリウムエチルスルフェート、1−ブチル−3−メチルイミダゾリウムクロリド、1−ブチル−3−メチルイミダゾリウムメタンスルホネート、1−エチル−3−メチルイミダゾリウムクロリド、1−エチル−3−メチルイミダゾリウムチオシアネート及び1−ブチル−3−メチルイミダゾリウムチオシアネートからなる群から選択される有機イオン液体であって、大気圧(1バール)で180℃未満の融点を有する塩である有機イオン液体の混合物を含む、組成物であって、
ポリエチレン及びそのコポリマー、ポリプロピレン及びそのコポリマー並びにスチレン及びそのコポリマーからなる群から選択される熱可塑性ポリマー中に導入される、前記組成物。
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JP2009292944A (ja) | 2008-06-05 | 2009-12-17 | Toho Chem Ind Co Ltd | 帯電防止剤および帯電防止性熱可塑性樹脂組成物 |
CN102459442A (zh) | 2009-06-15 | 2012-05-16 | 巴斯夫欧洲公司 | 耐久抗静电添加剂组合物 |
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KR20120093429A (ko) | 2012-08-22 |
KR101778321B1 (ko) | 2017-09-13 |
CN102651981A (zh) | 2012-08-29 |
CN102651981B (zh) | 2015-05-27 |
TWI509060B (zh) | 2015-11-21 |
TW201137101A (en) | 2011-11-01 |
EP2509459A1 (en) | 2012-10-17 |
US8993660B2 (en) | 2015-03-31 |
WO2011069960A1 (en) | 2011-06-16 |
US20120283367A1 (en) | 2012-11-08 |
JP2013513676A (ja) | 2013-04-22 |
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