JP2013509456A - 高い絶縁抵抗を有する熱可塑性ポリウレタン組成物 - Google Patents
高い絶縁抵抗を有する熱可塑性ポリウレタン組成物 Download PDFInfo
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- JP2013509456A JP2013509456A JP2012535576A JP2012535576A JP2013509456A JP 2013509456 A JP2013509456 A JP 2013509456A JP 2012535576 A JP2012535576 A JP 2012535576A JP 2012535576 A JP2012535576 A JP 2012535576A JP 2013509456 A JP2013509456 A JP 2013509456A
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- 238000010128 melt processing Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
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- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- FATBGEAMYMYZAF-KTKRTIGZSA-N oleamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(N)=O FATBGEAMYMYZAF-KTKRTIGZSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- FATBGEAMYMYZAF-UHFFFAOYSA-N oleicacidamide-heptaglycolether Natural products CCCCCCCCC=CCCCCCCCC(N)=O FATBGEAMYMYZAF-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000004209 oxidized polyethylene wax Substances 0.000 description 1
- 235000013873 oxidized polyethylene wax Nutrition 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- VGTPKLINSHNZRD-UHFFFAOYSA-N oxoborinic acid Chemical compound OB=O VGTPKLINSHNZRD-UHFFFAOYSA-N 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003012 phosphoric acid amides Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- LVEOKSIILWWVEO-UHFFFAOYSA-N tetradecyl 3-(3-oxo-3-tetradecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCC LVEOKSIILWWVEO-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L75/04—Polyurethanes
- C08L75/08—Polyurethanes from polyethers
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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
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- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
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- H—ELECTRICITY
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- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/17—Protection against damage caused by external factors, e.g. sheaths or armouring
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/17—Protection against damage caused by external factors, e.g. sheaths or armouring
- H01B7/29—Protection against damage caused by extremes of temperature or by flame
- H01B7/295—Protection against damage caused by extremes of temperature or by flame using material resistant to flame
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- C—CHEMISTRY; METALLURGY
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/016—Flame-proofing or flame-retarding additives
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- 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
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- C—CHEMISTRY; METALLURGY
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- 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
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- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
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- Compositions Of Macromolecular Compounds (AREA)
- Organic Insulating Materials (AREA)
- Insulated Conductors (AREA)
- Inorganic Insulating Materials (AREA)
Abstract
Description
「熱可塑性ポリウレタン」(又は「TPU」)は、本明細書で用いているように、ジ−イソシアネート、1つ又は複数のポリマージオール及び任意選択で1つ又は複数の二官能連鎖延長剤の反応生成物である。TPUは、プレポリマー、準プレポリマー又はワンショット法により調製することができる。ジ−イソシアネートは、TPUにおけるハードセグメントを形成し、芳香族、脂肪族若しくは脂環式ジ−イソシアネート又はこれらの化合物の2つ以上の組合せであってよい。ジ−イソシアネート(OCN−R−NCO)由来の構造単位の非限定的な例は、以下の式(I)
本組成物中の金属水和物は、組成物に難燃特性を付与する。適切な例は、三水酸化アルミニウム(ATH又はアルミニウム三水和物としても公知である)及び水酸化マグネシウム(二水酸化マグネシウムとしても公知である)を含むが、これらに限定されない。金属水酸化物は、天然のものでも合成のものでもよい。
IR特性を有するリン系難燃剤は、組成物に湿潤時(wet)IR特性を含む高度IR特性を付与することができる。重要なことに、これは、後述する実施例により例示するように、すべてのリン系難燃剤の固有又は一般的な特性であるとは限らない。ビスフェノールAジホスフェート(BPADP)は、本組成物にIR特性を付与するリン系難燃剤の一例である。
金属水和物及びIR特性を有する少なくとも1つのリン系難燃剤に加えて、その他の難燃剤を組成物に場合によって含めることができる。組成物に含めることができるその他のリン系難燃剤は、有機ホスホン酸、ホスホン酸エステル、ホスフィン酸エステル、亜ホスホン酸エステル、亜ホスフィン酸エステル、ホスフィンオキシド、ホスフィン、亜リン酸エステル又はリン酸エステル、リンエステルアミド、リン酸アミド、ホスホン酸アミド及びホスフィン酸アミドを含むが、これらに限定されない。組成物中に存在する難燃剤は、ハロゲンフリーの組成物を提供することができるように、望ましくはハロゲンフリーである。「ハロゲンフリー」及びこれに類する用語は、組成物がハロゲンを含有しない又は実質的に含有しない、すなわち、イオンクロマトグラフィー(IC)又は類似の分析方法により測定するとき2000mg/kg未満のハロゲンを含有することを意味する。この量より少ないハロゲン含量は、例えば、ワイヤ又はケーブル被覆としての組成物の有効性に対して重要でないとみなされる。
本組成物は、燃焼時のしたたりを予防又は最小限にするために1つ又は複数のチャー形成剤を場合によって含み得る。例えば、組成物のいくつかの実施形態は、エポキシ化ノボラック樹脂をチャー形成剤として含む。「エポキシ化ノボラック樹脂」は、有機溶媒中のエピクロロヒドリンとフェノールノボラックポリマーとの反応生成物である。適切な有機溶媒の非限定的な例としては、アセトン、メチルエチルケトン、メチルアミルケトン及びキシレンなどがある。エポキシ化ノボラック樹脂は、液体、半固体、固体及びそれらの組合せであってよい。
組成物は、添加剤及び/又は充填剤も場合によって含有し得る。代表的な添加剤は、抗酸化剤、溶融加工熱安定剤、加水分解安定性向上剤、加工助剤、着色剤、カップリング剤、紫外線安定剤(UV吸収剤を含む)、帯電防止剤、核形成剤、スリップ剤、可塑剤、滑沢剤、粘度調整剤、粘着付与剤、ブロッキング防止剤、界面活性剤、エクステンダー油、酸掃去剤及び金属不活性化剤を含むが、これらに限定されない。これらの添加剤は、一般的に従来の様式で、且つ、例えば、組成物の重量に基づいて0.01重量%以下から10重量%以上までの従来の量で用いる。
上記のように、本組成物は、高度絶縁抵抗を特徴とする。本開示の目的のために、IR及び湿潤時IRは、後述する実施例でより詳細に述べるように、UL 62規格に従って測定する。いくつかの実施形態において、本組成物は、少なくとも3GΩ.mのIRを有する。これは、少なくとも3.5GΩ.mのIRを有する組成物を含み、少なくとも3.9GΩ.mのIRを有する組成物をさらに含む。いくつかの実施形態において、本組成物は、少なくとも2.5GΩ.mの湿潤時IRを有する。これは、組成物が少なくとも3GΩ.mの湿潤時IRを有する実施形態を含む。
それらの優れた絶縁抵抗特性に加えて、本組成物は、良好な難燃特性を示す。したがって、本組成物のいくつかの実施形態は、それらがVW−1と分類されることを特徴とする。「VW−1」は、ワイヤ及びスリーブのUnderwriters’ Laboratory(UL)難燃性である。これは、UL 1441規格のもとにワイヤ又はスリーブが与えられ得る最高の難燃性である「垂直ワイヤ、クラス1(Vertical Wire, Class 1)」を意味する。試験は、ワイヤ又はスリーブを垂直位置におくことによって実施される。炎をその下に一定の時間つけておき、次いで除去する。次いでスリーブの特徴を記録する。VW−1耐炎試験は、UL−1581の方法1080に従って判定される。
本組成物は、UL 1581−2001に従って、そして後述する実施例でより詳細に述べるように測定するとき、良好な熱変形特性を示し得る。いくつかの実施形態において、本組成物は、30%以下の150℃変形を有する。これは、25%以下の150℃変形を有する組成物を含む。
組成物の配合は、当業者に公知の標準的装置により行うことができる。配合装置の例は、Banbury(商標)又はBolling(商標)密閉混合機などのバッチ式密閉混合機である。或いは、Farrel(商標)連続式混合機、Werner and Pfleiderer(商標)二軸混合機又はBuss(商標)混練連続押出機などの連続式一又は二軸混合機を用いることができる。
本発明の他の態様は、本発明の1つ又は複数の組成物を含む、成形又は押出成形物品などの物品を提供する。
以下の実施例に本発明による熱可塑性ポリマー組成物を作製する方法の実施形態を示す。
これらの実施例で用いたTPUは、ポリエーテル熱可塑性ポリウレタンであるPELLETHANE(商標)2103−90 AE(Lubrizol Advanced Materialsから入手できる)である。使用前に、TPU試料を真空中で90℃で少なくとも4時間予備乾燥する。Adekaから入手した等級名FP600を有するビス(リン酸ジフェニル)(BPADP)は、受け取ったままの状態で用いる。Showa Denkaから入手したアルミニウム水和物は、100℃で6時間予備乾燥する。
表Aに示す組成物は、二軸押出機で調製する。組成物の調製は、以下の記述に従って行う。TPUを高速混合機に加える。酸化アルミニウム三水和物充填剤の一部を加え、10秒間混合する。次に残りの酸化アルミニウム三水和物をBPADPとともに混合物に加える。予熱したエポキシ化ノボラックをさじを用いて混合機に徐々に入れる。次に、Irganox 1010及びIrgafos 168添加剤を加える。すべての成分を混合機に加えたとき、得られた混合物を1800RPMで1分間混合する。次に、予備混合された配合物を混合機から除去し、190℃未満のバレル温度、35.5mmの軸直径及び38.6のLID(長さ対直径比)を有し、生産高が約20kg/時間の二軸押出機により押出成形する。得られるペレットを120℃で6時間乾燥する。
組成物は、以下の試験及び規格によるそれらのIR、湿潤時IR、熱変形、引張特性、熱老化特性及び耐燃性により特徴づけられる。
絶縁抵抗を試験するのに用いるワイヤ試料は、単一コード(single cord)である。単一コードワイヤは、溶融組成物の1層を銅導体の周りに被覆するためのBrabenderワイヤ被覆ユニットを用いて作製する。IR及び湿潤時IRの測定は、UL 62規格に従って耐電圧試験器(Dongguan Yuehua Electric Industrial Co.,Ltd、China)により行う。10メートル(m)の長さを有する単一コードを試験に用いる。コードの両端をはがして銅線を露出させる。IR試験のために、500V DCを空気中の導体と試験電極との間に印加し、1分後にIRを測定する。湿潤時IR試験のために、コードをあらかじめ接地した透明な水に少なくとも1時間浸す。500V DC電圧を水中の導体と高電圧電極との間に印加し、浸したまま1分後に湿潤時IR値を測定する。
熱変形試験は、UL 1581−2001規格に従って行う。各製剤について、2つの並行試料プラーク(plaque)をオーブンに入れ、150℃で1時間予熱する。次いで予熱済み試料を同じ荷重を用いて150℃で1時間プレスする。プレスした試料を荷重を除去せずに23℃の設定温度のASTM室にさらに1時間入れる。試料プラークの厚さの変化を記録し、熱変形(HD)をHD%=(D0−D1)/D0 *100%により計算する。ここで、D0は、最初の試料の厚さを表し、D1は、変形過程後の試料の厚さを表す。2つの並行試料について計算された変形を平均する。
引張試験は、Instron引張試験機(5565型)を用いてASTM D 638に従って500mm/分の速度で行う。プラーク試料(ASTM D 638 1型引張棒材165×12.7×3.18mm)は、FANUC100トン高速射出成形機により調製する。
熱老化試験は、UL 1581に従って行う。試料を最初に完全ドラフト空気循環オーブン(full-draft circulating-air oven)中で121.0±1.0℃で168時間老化させ、次いでInstronの機械によりASTM D 638に従って試験する。保持率は、保持率%=老化/非老化*100%により計算する。
Mimic VW−1 FR試験をUL 94チャンバー内で行う。試験検体は、200*2.7*1.9mmの寸法に制限する。検体は、下端に50gの荷重をかけることにより長軸を鉛直にしてクランプに吊り下げる。紙フラッグ(2*0.5cm)をワイヤの上部に取り付ける。炎の下部(バーナーオラクルの最高点)からフラッグの下部までの距離は、18cmである。炎は、45秒間連続して当てる。フレーム時間後(after flame time)(AFT)、非炭化ワイヤ長(UCL)及び非炭化フラッグ面積百分率(非炭化のフラッグ)を燃焼時及び後に記録する。4つ又は5つの検体を各試料について試験する。次の現象のいずれかがあれば、「不合格」の分類となる。(1)検体の下の綿に着火する;(2)フラッグが燃え尽きる;且つ/又は(3)炎によるしたたりがある。
表Aにレゾルシノールジフェニルリン酸(RDP)を有機難燃剤として用いる比較実施例の製剤及びBPADPを難燃剤として用いる本発明の実施例の製剤を示す。表1に両製剤の測定された特性も報告する。第1列は、比較実施例が不良なIR性能並びに熱老化引張伸び保持率を有することを示している。第2列は、本発明の実施例が著しく改善されたIR、湿潤時IR及び熱老化特性並びに燃焼性能、150℃熱変形及び機械的特性の良好なバランスをもたらすことを示している。
Claims (10)
- (a)熱可塑性ポリウレタンと、
(b)金属水和物難燃剤と、
(c)絶縁抵抗特性を有するリン系難燃剤と
を含む組成物であって、UL 94難燃剤規格に合格し、UL 62により測定するとき少なくとも3GΩ.mの絶縁抵抗を有することを特徴とする、組成物。 - UL 62により測定するとき少なくとも3.5GΩ.mの絶縁抵抗を有する、請求項1に記載の組成物。
- 前記絶縁抵抗特性を有するリン系難燃剤がビスフェノールAジホスフェートである、請求項2に記載の組成物。
- チャー形成剤をさらに含む、請求項1に記載の組成物。
- 前記チャー形成剤がエポキシノボラックである、請求項4に記載の組成物。
- 組成物の総重量に基づいて少なくとも30重量パーセントの金属水和物難燃剤及び組成物の総重量に基づいて少なくとも5重量パーセントのビスフェノールAジホスフェートを含む、請求項3に記載の組成物。
- 組成物の総重量に基づいて30〜40重量パーセントの金属水和物難燃剤及び組成物の総重量に基づいて10〜20重量パーセントのビスフェノールAジホスフェートを含む、請求項3に記載の組成物。
- 前記金属水和物難燃剤が水酸化アルミニウムである、請求項3に記載の組成物。
- 請求項1に記載の組成物で少なくとも部分的に被覆された絶縁導電性ワイヤ。
- 請求項7に記載の組成物で少なくとも部分的に被覆された絶縁導電性ワイヤ。
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EP2493982A1 (en) | 2012-09-05 |
US20120202061A1 (en) | 2012-08-09 |
MX2012005035A (es) | 2012-05-22 |
KR20120083918A (ko) | 2012-07-26 |
CA2778120A1 (en) | 2011-05-05 |
MX347796B (es) | 2017-05-12 |
TW201139629A (en) | 2011-11-16 |
EP2493982B1 (en) | 2018-07-18 |
BR112012009785B1 (pt) | 2021-03-02 |
CN102686672B (zh) | 2014-03-12 |
BR112012009785A2 (pt) | 2020-08-25 |
WO2011050520A1 (en) | 2011-05-05 |
EP2493982A4 (en) | 2014-05-28 |
CN102686672A (zh) | 2012-09-19 |
KR101652561B1 (ko) | 2016-08-30 |
CA2778120C (en) | 2016-10-25 |
JP5499177B2 (ja) | 2014-05-21 |
US9527998B2 (en) | 2016-12-27 |
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