JP2013508474A - 静電散逸性tpuおよびその組成物 - Google Patents
静電散逸性tpuおよびその組成物 Download PDFInfo
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- JP2013508474A JP2013508474A JP2012534217A JP2012534217A JP2013508474A JP 2013508474 A JP2013508474 A JP 2013508474A JP 2012534217 A JP2012534217 A JP 2012534217A JP 2012534217 A JP2012534217 A JP 2012534217A JP 2013508474 A JP2013508474 A JP 2013508474A
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- Prior art keywords
- composition
- diisocyanate
- acid
- glycol
- esd
- Prior art date
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- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 100
- 229920002803 thermoplastic polyurethane Polymers 0.000 claims abstract description 64
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 61
- 229920000642 polymer Polymers 0.000 claims abstract description 43
- 229920005906 polyester polyol Polymers 0.000 claims abstract description 39
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000004970 Chain extender Substances 0.000 claims abstract description 27
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 22
- 239000004433 Thermoplastic polyurethane Substances 0.000 claims abstract description 10
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 9
- 150000002148 esters Chemical class 0.000 claims abstract description 6
- -1 polyoxymethylene Polymers 0.000 claims description 40
- 150000003839 salts Chemical class 0.000 claims description 28
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 27
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 23
- 229910052751 metal Inorganic materials 0.000 claims description 22
- 239000002184 metal Substances 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 21
- 229920000570 polyether Polymers 0.000 claims description 20
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 18
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 11
- 229920005601 base polymer Polymers 0.000 claims description 10
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 9
- 239000001361 adipic acid Substances 0.000 claims description 9
- 235000011037 adipic acid Nutrition 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 8
- 229920005862 polyol Polymers 0.000 claims description 7
- 150000003077 polyols Chemical class 0.000 claims description 7
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- 238000010276 construction Methods 0.000 claims description 5
- 239000000446 fuel Substances 0.000 claims description 5
- 239000004800 polyvinyl chloride Substances 0.000 claims description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004801 Chlorinated PVC Substances 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 4
- 229920000457 chlorinated polyvinyl chloride Polymers 0.000 claims description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 4
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 claims description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 3
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 claims description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 3
- 239000004035 construction material Substances 0.000 claims description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 3
- 229910001416 lithium ion Inorganic materials 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 229920006324 polyoxymethylene Polymers 0.000 claims description 3
- 229920006380 polyphenylene oxide Polymers 0.000 claims description 3
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 3
- PMDHMYFSRFZGIO-UHFFFAOYSA-N 1,4,7-trioxacyclotridecane-8,13-dione Chemical compound O=C1CCCCC(=O)OCCOCCO1 PMDHMYFSRFZGIO-UHFFFAOYSA-N 0.000 claims description 2
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 claims description 2
- ICLCCFKUSALICQ-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanato-3-methylphenyl)-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(C=2C=C(C)C(N=C=O)=CC=2)=C1 ICLCCFKUSALICQ-UHFFFAOYSA-N 0.000 claims description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 2
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004252 FT/ICR mass spectrometry Methods 0.000 claims description 2
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 2
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 claims description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 claims description 2
- 229940106012 diethylene glycol adipate Drugs 0.000 claims description 2
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical compound OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000005518 polymer electrolyte Substances 0.000 claims description 2
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- 239000004065 semiconductor Substances 0.000 claims description 2
- 230000004580 weight loss Effects 0.000 claims description 2
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 claims 1
- 239000005058 Isophorone diisocyanate Substances 0.000 claims 1
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims 1
- 239000005022 packaging material Substances 0.000 claims 1
- 239000004753 textile Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 229920002959 polymer blend Polymers 0.000 abstract description 3
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- 239000000543 intermediate Substances 0.000 description 36
- 239000000654 additive Substances 0.000 description 21
- 239000000463 material Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000000376 reactant Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 230000000704 physical effect Effects 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
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- 125000003118 aryl group Chemical group 0.000 description 7
- 150000002334 glycols Chemical class 0.000 description 7
- QSZMZKBZAYQGRS-UHFFFAOYSA-N lithium;bis(trifluoromethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F QSZMZKBZAYQGRS-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- 125000001931 aliphatic group Chemical group 0.000 description 5
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- 229910019142 PO4 Inorganic materials 0.000 description 4
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- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
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- 238000000576 coating method Methods 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
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- MCVFFRWZNYZUIJ-UHFFFAOYSA-M lithium;trifluoromethanesulfonate Chemical compound [Li+].[O-]S(=O)(=O)C(F)(F)F MCVFFRWZNYZUIJ-UHFFFAOYSA-M 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
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- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
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- 229910052755 nonmetal Inorganic materials 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
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- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
Description
本発明に使用される静電散逸性熱可塑性ポリウレタン(ESD−TPU)ポリマーは、3種類の反応物の反応によって作製される。第1の反応物はポリエステルポリオール中間体であり、第2の反応物はジイソシアナートであり、第3の反応物は鎖伸長剤である。3種類の反応物の各々を以下に考察する。
本発明のポリエステルポリオール中間体は、少なくとも1種類のジアルキレングリコールと少なくとも1種類のジカルボン酸またはそのエステルまたは無水物から誘導される。
本発明のESD−TPUを作製するための第2の反応物は、ジイソシアナートである。適切なジイソシアナートとしては、(i)4,4’−メチレンビス−(フェニルイソシアナート)(MDI)、m−キシリレンジイソシアナート(XDI)、フェニレン−1,4−ジイソシアナート、1,5−ナフタレンジイソシアナート、ジフェニルメタン−3,3’−ジメトキシ−4,4’−ジイソシアナート(TODI)、トルエンジイソシアナート(TDI)などの芳香族ジイソシアナート、および(ii)イソホロンジイソシアナート(IPDI)、1,4−シクロヘキシルジイソシアナート(CHDI)、デカン−1,10−ジイソシアナート、ヘキサメチレンジイソシアナート(HDI)、ジシクロヘキシルメタン−4,4’−ジイソシアナートなどの脂肪族ジイソシアナートが挙げられる。一部の実施形態においては、ジイソシアナートは4,4’−メチレンビス(フェニルイソシアナート)(MDI)である。別の実施形態においては、列挙したジイソシアナートの1種類以上を本発明から除外することができる。
適切な鎖伸長剤としてはグリコールが挙げられ、脂肪族、芳香族またはその組合せとすることができる。一部の実施形態においては、鎖伸長剤は、2から約12個の炭素原子を有するグリコールである。
3種類の反応物(ポリエステルポリオール中間体、ジイソシアナートおよび鎖伸長剤)を互いに反応させて、本発明の高分子量ESD−TPUを形成する。3種類の反応物を反応させる任意の公知プロセスを使用してTPUを作製することができる。一実施形態においては、プロセスは、いわゆる「一括」プロセスであり、全3種類の反応物を押出機反応器に添加し、反応させる。ヒドロキシル含有成分、すなわち、ポリエステルポリオール中間体および鎖伸長剤グリコールの総当量に対するジイソシアナートの当量は、約0.95から約1.10、または約0.96から約1.02、更には約0.97から約1.005である。ウレタン触媒を利用する反応温度は、約175℃から約245℃とすることができ、別の実施形態においては180℃から220℃とすることができる。
一部の実施形態においては、本発明の組成物は、金属含有塩、塩複合体、または金属イオンと非金属イオンもしくは分子の結合によって形成される塩化合物を更に含むことができる。存在する塩の量は、ESD−TPUポリマーおよび/または組成物全体のESD特性を改善するのに有効な量とすることができる。任意に選択される塩成分を一括重合プロセス中に添加することができる。塩は、リチウム含有塩とすることができる。
本発明の組成物は、追加の有用な添加剤を更に含むことができ、かかる添加剤を適切な量で利用することができる。これらの任意に選択される追加の添加剤としては、所望のとおりに、不透明化顔料、着色剤、鉱物および/または不活性充填剤、光安定剤を含めた安定剤、潤滑剤、UV吸収剤、加工助剤、酸化防止剤、オゾン分解防止剤、ならびに他の添加剤が挙げられる。有用な不透明化顔料としては、二酸化チタン、酸化亜鉛、およびチタナートイエローが挙げられる。有用な着色顔料としては、カーボンブラック、黄色酸化物、褐色酸化物、ローおよびバーントシエナまたはアンバー、酸化クロムグリーン、カドミウム顔料、クロム顔料、ならびに他の混合金属酸化物および有機顔料が挙げられる。有用な充填剤としては、珪藻土(superfloss)クレイ、シリカ、タルク、マイカ、珪灰石(wallostonite)、硫酸バリウムおよび炭酸カルシウムが挙げられる。必要に応じて、酸化防止剤などの有用な安定剤を使用することができ、フェノール酸化防止剤が挙げられる。有用な光安定剤としては有機リン酸および有機スズチオラート(メルカプチド)が挙げられる。有用な潤滑剤としては、ステアリン酸金属、パラフィン油およびアミドワックスが挙げられる。有用なUV吸収剤としては、2−(2’−ヒドロキシフェニル)ベンゾトリアゾールおよび2−ヒドロキシベンゾフェノンが挙げられる。添加剤は、TPUポリマーの加水分解安定性を改善するのに使用することもできる。これらの任意に選択される追加の上記添加剤の各々は、本発明の組成物中に存在することができ、または本発明の組成物から除外することができる。
本発明のESD−TPUポリマーは、マトリックスまたはベースポリマーとブレンドしてポリマーブレンドを形成することができる。このブレンドは、上記塩変性ESD−TPUポリマーを使用して作製することもできる。
(ii)ポリスチレン(PS)、アクリロニトリルブタジエンスチレン(ABS)、スチレンアクリロニトリル(SAN)、スチレンブタジエンゴム(SBRまたはHIPS)、ポリアルファメチルスチレン、メタクリル酸メチルスチレン(MS)、スチレン無水マレイン酸(SMA)、(スチレン−ブタジエン−スチレンコポリマー(SBS)、スチレン−エチレン/ブタジエン−スチレンコポリマー(SEBS)などの)スチレン−ブタジエンコポリマー(SBC)、スチレン−エチレン/プロピレン−スチレンコポリマー(SEPS)、スチレンブタジエンラテックス(SBL)、エチレンプロピレンジエンモノマー(EPDM)および/またはアクリルエラストマーで変性されたSAN(例えば、PS−SBRコポリマー)、その組合せなどのスチレン系(styrenic)、
(iii)熱可塑性ポリウレタン(TPU)、
(iv)ポリアミド6,6(PA66)、ポリアミド1,1(PA11)、ポリアミド1,2(PA12)を含めたナイロン(商標)、コポリアミド(COPA)、その組合せなどのポリアミド、
(v)ポリアクリル酸メチル、ポリメタクリル酸メチル、その組合せなどのアクリルポリマー、
(vi)ポリ塩化ビニル(PVC)、塩素化ポリ塩化ビニル(CPVC)またはその組合せ、
(vii)ポリアセタールなどのポリオキシメチレン、
(viii)ポリエチレンテレフタラート(PET)、ポリブチレンテレフタラート(PBT)、グリコール変性ポリエチレンテレフタラート(PETG)などのポリエーテル−エステルブロックコポリマーを含めたコポリエステルおよび/またはポリエステルエラストマー(COPE)、ポリ乳酸(PLA)、その組合せなどのポリエステル、
(ix)ポリカルボナート(PC)、ポリフェニレンスルフィド(PPS)、ポリフェニレンオキシド(PPO)またはその組合せ、
またはその組合せ。
本発明の組成物は、上記ブレンドを含めて、種々の用途に有用である。幾つかの例は、チューブ、用紙トレイ、床タイル、機械ハウジング、建設および製造装置、ならびにポリマーシートおよびフィルムである。より具体的には、例としては、燃料ライン、蒸気回収装置などの燃料取扱い装置、事務機器、クリーンルーム、建設区域などの床のコーティング、用途、衣類、床材、マット、電子部品実装およびハウジングを含めたクリーンルーム装置、チップホルダー、チップレール、輸送箱および輸送箱上面、医学的用途、デバイダーおよび/またはセパレーターなどの電池部品、ならびに一般成形物品が挙げられる。
上記様式で、一括プロセスを使用して、スズ触媒の存在下で、4,4’−メチレンビス−(フェニルイソシアナート)、ベンゼングリコール、およびジエチレングリコールとアジピン酸から誘導されるポリエステルポリオール中間体を反応させることによってESD TPUを調製する。
金属含有塩であるリチウムトリフルオロメタンスルホンイミド1.9百分率部(phr)を湿式吸収によってTPUにドープする以外は実施例1−Aの手順に従ってESD TPUを調製する。
金属含有塩であるトリフルオロメタンスルホン酸のリチウム塩1.4phrを湿式吸収によってTPUにドープする以外は実施例1−Aの手順に従ってESD TPUを調製する。
金属含有塩であるトリフルオロメタンスルホン酸のリチウム塩1.3phrを湿式吸収によってTPUにドープする以外は実施例1−Aの手順に従ってESD TPUを調製する。
上記様式で、一括プロセスを使用して、スズ触媒の存在下で、4,4’−メチレンビス−(フェニルイソシアナート)、1,4−ブタンジオール、およびジエチレングリコールとアジピン酸から誘導されるポリエステルポリオール中間体を反応させることによってESD TPUを調製する。
金属含有塩であるリチウムトリフルオロメタンスルホンイミド1.9phrを湿式吸収によってTPUにドープする以外は実施例2−Aの手順に従ってESD TPUを調製する。
金属含有塩であるトリフルオロメタンスルホン酸のリチウム塩1.4phrを湿式吸収によってTPUにドープする以外は実施例2−Aの手順に従ってESD TPUを調製する。
比較例3−A
市販ESDポリエーテルTPUを本発明の組成物との比較のために使用する。この例は、Lubrizol Advanced Materials, Inc.から入手可能なESDポリエーテルTPUであるStat−Rite(商標)C−2300である。
1,4−ブタンジオールとアジピン酸から調製されるポリエステルポリオール中間体92.4pbw、ジエチレングリコールとアジピン酸から調製されるポリエステルポリオール中間体92.4pbw、ベンゼングリコール14.2pbw、4,4’−メチレンビス−(フェニルイソシアナート)43.4pbw、リチウムトリフルオロメタンスルホンイミド24.3pbw、およびオクタン酸スズ1滴を化合させるin situ重合によってESD TPUを調製する。
処理中にビス(パーフルオロメタン)スルホンイミドアルキルアンモニウム塩を含むイオン性液体73.0pbwを材料に添加する以外は、実施例4−Aの手順に従ってESD TPUを調製する。
1,4−ブタンジオールとアジピン酸から調製されるポリエステルポリオール中間体92.4pbw、ジエチレングリコールとアジピン酸から調製されるポリエステルポリオール中間体92.4pbw、ベンゼングリコール14.2pbw、4,4’−メチレンビス−(フェニルイソシアナート)43.4pbw、およびジ−プロピレングリコール0.75pbwを化合させるin situ重合によってESD TPUを調製する。
処理中にリチウムトリフルオロメタンスルホンイミド2.0pbwを材料に添加する以外は、実施例5−Aの手順に従ってESD TPUを調製する。上述したように、TPUの一括重合中に塩を添加する。
処理中にリチウムトリフルオロメタンスルホンイミド3.0pbwを材料に添加する以外は、実施例5−Bの手順に従ってESD TPUを調製する。
処理中にリチウムトリフルオロメタンスルホンイミド3.5pbwを材料に添加する以外は、実施例5−Bの手順に従ってESD TPUを調製する。
Claims (15)
- (a)少なくとも1種類のポリエステルポリオール中間体を(b)少なくとも1種類のジイソシアナートおよび(c)少なくとも1種類の鎖伸長剤と反応させることによって作製される静電散逸性熱可塑性ポリウレタン組成物であって、
(a)前記ポリエステルポリオール中間体が、少なくとも1種類のジアルキレングリコールと少なくとも1種類のジカルボン酸またはそのエステルまたは無水物から誘導される中間体を含む、組成物。 - 前記ジカルボン酸が4から15個の炭素原子を含み、そして前記ジアルキレングリコールが2から8個の炭素原子を含む、請求項1に記載の組成物。
- 前記ジカルボン酸が、コハク酸、グルタル酸、アジピン酸、ピメリン酸、スベリン酸、アゼライン酸、セバシン酸、ドデカン二酸、イソフタル酸、テレフタル酸、シクロヘキサンジカルボン酸またはその組合せを含み、そして、
前記ジアルキレングリコールが、オキシジメタノール、ジエチレングリコール、ジプロピレングリコール、3,3−オキシジプロパン−1−オール、ジブチレングリコールまたはその組合せを含む、請求項1から2のいずれかに記載の組成物。 - (b)前記ジイソシアナートが、4,4’−メチレンビス−(フェニルイソシアナート)、ヘキサメチレンジイソシアナート、3,3’−ジメチルビフェニル−4,4’−ジイソシアナート、m−キシリレンジイソシアナート、フェニレン−1,4−ジイソシアナート、ナフタレン−1,5−ジイソシアナート、ジフェニルメタン−3,3’−ジメトキシ−4,4’−ジイソシアナート、トルエンジイソシアナート、イソホロンジイソシアナート、1,4−シクロヘキシルジイソシアナート、デカン−1,10−ジイソシアナート、ジシクロヘキシルメタン−4,4’−ジイソシアナートまたはその組合せを含み、そして、
(c)前記鎖伸長剤が、エチレングリコール、ジエチレングリコール、プロピレングリコール、ジプロピレングリコール、1,4−ブタンジオール、1,6−ヘキサンジオール、1,3−ブタンジオール、1,5−ペンタンジオール、1,4−シクロヘキサン−ジメタノール、ヒドロキノンジ(ヒドロキシエチル)エーテル、ネオペンチルグリコール、1,4−ビス(2−ヒドロキシエトキシ)ベンゼンまたはその組合せを含む、請求項1から3のいずれかに記載の組成物。 - (a)前記ポリエステルポリオール中間体がポリ(ジエチレングリコールアジパート)を含み、(b)前記ジイソシアナートが4,4’−メチレンビス−(フェニルイソシアナート)を含み、そして、(c)前記鎖伸長剤がブタンジオール、ヒドロキノンジ(ヒドロキシエチル)エーテルまたはその組合せを含む、請求項1から4のいずれかに記載の組成物。
- 静電散逸のための有効量の金属含有塩を更に含む、請求項1から5のいずれかに記載の組成物。
- 前記金属含有塩がリチウム含有塩を含む、請求項6に記載の組成物。
- 前記組成物が以下の特性の少なくとも1つを有する、請求項1から7のいずれかに記載の組成物:
(i)前記組成物が、ASTM D−257によって測定して、1.0×1013Ω/□未満の表面抵抗率、および1.0×1012Ω・cm未満の体積抵抗率を有する、
(ii)前記組成物が、50%相対湿度で帯電プレートモニターを使用して測定して、1000Vから100Vまで約0.1秒未満の帯電圧減衰率を有し、そして前記組成物が、12%相対湿度でFTMS 101Cによって測定して、5000Vから50Vまでもしくは−5000Vから−50Vまで約0.1秒未満の帯電圧減衰率を有する。 - 前記組成物が以下の特性の少なくとも1つを有する、請求項1から8のいずれかに記載の組成物:
(i)前記組成物が、ASTM D−2240によって測定して少なくとも60ショアA単位の硬度を有する、
(ii)前記組成物が、ASTM D−412によって測定して、少なくとも10MPaの引張り強さ、および300%を超える極限伸びを有する、
(iii)前記組成物が、ダイCを使用してASTM D−624によって測定して、少なくとも5kg/mmのグレーブス引裂き値を有する、
(iv)前記組成物が、ASTM D−3389によって測定して1000回転当たり100mg未満のテーバー減量を有する、
(v)前記組成物が、少なくとも60,000の重量平均分子量を有する、
(vi)前記組成物が、ASTM D−1238手順Aによってバレル温度190℃および3.8kgピストン荷重で測定して50未満のメルトフローインデックスを有する。 - (a)前記ポリエステルポリオール成分がポリエーテルポリオールを実質的に含まない、請求項1から9のいずれかに記載の組成物。
- 少なくとも1種類のベースポリマーを更に含む、請求項1から10のいずれかに記載の組成物。
- 前記ベースポリマーが、ポリオレフィン;スチレン系;熱可塑性ポリウレタン、ポリアミド;アクリルポリマー;ポリ塩化ビニル、塩素化ポリ塩化ビニル;ポリオキシメチレン;ポリエステル;ポリカルボナート;ポリフェニレンオキシド;ポリフェニレンスルフィド;またはその組合せを含む、請求項11に記載の組成物。
- 静電散逸性熱可塑性ポリウレタン組成物を作製するプロセスであって、(a)少なくとも1種類のポリエステル中間体を(b)少なくとも1種類のジイソシアナートおよび(c)少なくとも1種類の鎖伸長剤と反応させるステップを含み、(a)前記ポリエステル中間体が少なくとも1種類のジアルキレングリコールと少なくとも1種類のジカルボン酸またはそのエステルまたは無水物から誘導される、プロセス。
- 請求項1から12のいずれかに記載の静電散逸性熱可塑性ポリウレタン組成物を含む、成形されたポリマー物品。
- 前記物品が、ESDに感応性の半導体および電子部品のパッケージング材料;クリーンルーム装置および用途のための耐久または消耗部品;クリーンルームおよびデータセンター用の建設資材;繊維;積層シート;コンベヤベルト;医薬品;医療機器;電子部品;リチウムイオン電池の構築に使用されるセパレーター;リチウムポリマー電池および燃料電池の構築に使用されるポリマー電解質膜;またはその組合せを含む、請求項14に記載のポリマー物品。
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JP2021504510A (ja) * | 2017-11-22 | 2021-02-15 | ジーケイエヌ エアロスペース トランスパランシー システムズ インコーポレイテッド | 耐久性を備えた導電性ポリウレタン組成物および同組成物を塗布する方法 |
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JP2015505861A (ja) * | 2011-10-28 | 2015-02-26 | ルブリゾル アドバンスド マテリアルズ, インコーポレイテッド | 電気化学セルのためのポリウレタンに由来する膜および/またはセパレーター |
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JP2021504510A (ja) * | 2017-11-22 | 2021-02-15 | ジーケイエヌ エアロスペース トランスパランシー システムズ インコーポレイテッド | 耐久性を備えた導電性ポリウレタン組成物および同組成物を塗布する方法 |
JP7383612B2 (ja) | 2017-11-22 | 2023-11-20 | ジーケイエヌ エアロスペース トランスパランシー システムズ インコーポレイテッド | 耐久性を備えた導電性ポリウレタン組成物および同組成物を塗布する方法 |
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KR101762327B1 (ko) | 2017-07-27 |
MY164067A (en) | 2017-11-15 |
WO2011046756A1 (en) | 2011-04-21 |
JP5584303B2 (ja) | 2014-09-03 |
EP2488564B1 (en) | 2016-12-07 |
TWI523880B (zh) | 2016-03-01 |
TW201125886A (en) | 2011-08-01 |
US9012590B2 (en) | 2015-04-21 |
KR20120095919A (ko) | 2012-08-29 |
CN102597038A (zh) | 2012-07-18 |
US10000624B2 (en) | 2018-06-19 |
EP2488564A1 (en) | 2012-08-22 |
US20110092648A1 (en) | 2011-04-21 |
US20150340675A1 (en) | 2015-11-26 |
ES2609766T3 (es) | 2017-04-24 |
US20170015815A1 (en) | 2017-01-19 |
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