JP5508013B2 - オリゴマー状のビスホスフェート難燃剤およびこれを含有する組成物 - Google Patents
オリゴマー状のビスホスフェート難燃剤およびこれを含有する組成物 Download PDFInfo
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- JP5508013B2 JP5508013B2 JP2009526738A JP2009526738A JP5508013B2 JP 5508013 B2 JP5508013 B2 JP 5508013B2 JP 2009526738 A JP2009526738 A JP 2009526738A JP 2009526738 A JP2009526738 A JP 2009526738A JP 5508013 B2 JP5508013 B2 JP 5508013B2
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- 239000003063 flame retardant Substances 0.000 title claims description 34
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims description 23
- 239000000203 mixture Substances 0.000 title claims description 18
- 125000005340 bisphosphate group Chemical group 0.000 title description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 40
- 239000004417 polycarbonate Substances 0.000 claims description 30
- 229920000515 polycarbonate Polymers 0.000 claims description 29
- 239000011342 resin composition Substances 0.000 claims description 27
- 229910019142 PO4 Inorganic materials 0.000 claims description 24
- 239000010452 phosphate Substances 0.000 claims description 20
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 16
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 15
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims description 14
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 9
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 6
- 230000009969 flowable effect Effects 0.000 claims description 6
- 229920005669 high impact polystyrene Polymers 0.000 claims description 6
- 239000004797 high-impact polystyrene Substances 0.000 claims description 6
- 229920006380 polyphenylene oxide Polymers 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 2
- 239000002131 composite material Substances 0.000 description 22
- 235000021317 phosphate Nutrition 0.000 description 20
- 239000000805 composite resin Substances 0.000 description 13
- OWICEWMBIBPFAH-UHFFFAOYSA-N (3-diphenoxyphosphoryloxyphenyl) diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1)(=O)OC1=CC=CC=C1 OWICEWMBIBPFAH-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 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 8
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000003301 hydrolyzing effect Effects 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- PWAYUHFEKDQEMK-UHFFFAOYSA-N benzene-1,4-diol;phosphoric acid Chemical compound OP(O)(O)=O.OP(O)(O)=O.OC1=CC=C(O)C=C1 PWAYUHFEKDQEMK-UHFFFAOYSA-N 0.000 description 5
- TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920002842 oligophosphate Polymers 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 150000004712 monophosphates Chemical class 0.000 description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ASONQZPECNCPCA-UHFFFAOYSA-N P(=O)(OC1(C(C=CC=C1)C)C)(OC1(C(C=CC=C1)C)C)OC1=CC(O)=CC=C1 Chemical compound P(=O)(OC1(C(C=CC=C1)C)C)(OC1(C(C=CC=C1)C)C)OC1=CC(O)=CC=C1 ASONQZPECNCPCA-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BQPNUOYXSVUVMY-UHFFFAOYSA-N [4-[2-(4-diphenoxyphosphoryloxyphenyl)propan-2-yl]phenyl] diphenyl phosphate Chemical compound C=1C=C(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 BQPNUOYXSVUVMY-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 239000000539 dimer Substances 0.000 description 3
- 238000005562 fading Methods 0.000 description 3
- -1 phosphate ester Chemical class 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000004429 Calibre Substances 0.000 description 2
- 229920004313 LEXAN™ RESIN 141 Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Polymers OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 2
- 0 **c(cc1)ccc1O Chemical compound **c(cc1)ccc1O 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- 239000004114 Ammonium polyphosphate Substances 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical class C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 description 1
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 1
- 229920004142 LEXAN™ Polymers 0.000 description 1
- 239000004418 Lexan Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 1
- 229920001276 ammonium polyphosphate Polymers 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000368 destabilizing effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000004431 polycarbonate resin Substances 0.000 description 1
- 229920005668 polycarbonate resin Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- GGRIQDPLLHVRDU-UHFFFAOYSA-M potassium;2-(benzenesulfonyl)benzenesulfonate Chemical compound [K+].[O-]S(=O)(=O)C1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 GGRIQDPLLHVRDU-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- 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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
- C08K5/5357—Esters of phosphonic acids cyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
Description
以下の表は、本発明に係る難燃性のオリゴマー状のヒドロキノンビス(ジフェニルホスフェート)の調製に使用した反応混合物を特定するものである。
ガラス反応器、凝縮器のための冷却機、および苛性スクラバー(caustic scrubber)システムを備えた反応熱量計。
ジフェニルクロロホスフェート、ヒドロキノンおよびMgCl2をN2雰囲気下で反応器に入れた。1時間かけてTR(反応温度)をゆっくり140℃に上昇させた。
実施例1に記載したのと同じ手順を使用して、本発明のオリゴマー状のヒドロキノンビス(ジフェニルホスフェート)(HDP)を調製した。このプロセスでは、モノフェニルジクロロホスフェート(MPCP)の添加を利用して、HPLCによって得た個々の構成要素であるオリゴホスフェートの割合を用いて公知の方法で決定した約1.15の平均n値を有するオリゴマー状の生成物(HDP)を生成させた。
UV安定性
難燃剤としてそれぞれFyrolflex RDP(n=1.28)、Fyrolflex BDP(n=1.14)、PX200(RXP)(n値は適用不可)および本発明の(実施例1で調製した)HDP(n=1.02)を含有するPC/ABS複合材を、同程度の可燃性(UL−94/V0、1.6mm 可燃性等級)を有する組成物へと配合した。これら複合材を押出し配合し、さらに射出成形プロセスで分散させた。これらの成形品で試験棒を調製し、促進UV曝露のためのQ−UVパネル試験に置いた。4つの複合材を、試験装置(Q−UVパネル試験機)中で約500時間(UV光のみ)、等しくUV照射に曝露した。曝露させた試料を、各試料の退色の程度について5人の人間によって目で見て判断し、最少の着色を伴う複合材に対する1(最良)および最も高い色変化を伴うコンパウンドに対する5(最悪)のポイント値を与えた。結果を以下の表に報告する。
加水分解安定性
ポリカーボネートは、特に酸性条件下で高熱および高湿度に曝されたとき、加水分解を受けやすい。従って、より良好な加水分解安定性を有する難燃剤は、ポリマー複合材を不安定化する効果がより小さい。ホスフェートエステルは、高熱および高湿度に敏感であり、酸種へと加水分解を受けてこれらの複合材の安定性に影響を及ぼす可能性がある。
熱変形温度
あらゆる工学的樹脂についての重要な特性の1つがその熱変形温度(HDT)値である。電子機器の動作で、標準的な家庭用電流または遠隔的にバッテリから電力供給を受ける電化製品で熱が生成される。複合材が所与の用途に対してあまりに低いHDT値を有する場合、プラスチック部は軟化して機器として役立たないものになるかも知れない。従って、より高いHDTを有するホスフェート組成物は、より低いHDT値を有するホスフェート複合材よりも好ましい。なぜなら、それは適切な材料を選択する際の重要なパラメータであることが多いためである。
FR−ポリカーボネート複合材の可燃性結果
Claims (8)
- nが1.02の平均値を有する、請求項1に記載のオリゴマー状のホスフェート。
- 前記樹脂が、スチレンポリマーおよびスチレンコポリマー、ポリフェニレンオキシド(PPO)、アクリロニトリルブタジエンスチレン(ABS)、ポリカーボネート(PC)、耐衝撃性ポリスチレン(HIPS)およびこれらの混合物からなる群から選択される、請求項3に記載の樹脂組成物。
- 前記樹脂がPC/ABSまたはPPO/HIPSである、請求項4に記載の樹脂組成物。
- 全組成物の2重量%〜20重量%の式Iのオリゴマー状のホスフェートまたはオリゴマー状のホスフェートの混合物難燃剤を含有する、請求項3から請求項5のいずれか1項に記載の樹脂組成物。
- 前記式Iのオリゴマー状の難燃剤がヒドロキノンビス(ジフェニルホスフェート)である、請求項3から請求項6に記載の樹脂組成物。
- 前記ヒドロキノンビス(ジフェニルホスフェート)が1.02の平均n値を有する、請求項7に記載の樹脂組成物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US84145906P | 2006-08-31 | 2006-08-31 | |
US60/841,459 | 2006-08-31 | ||
PCT/US2007/019172 WO2008027536A1 (en) | 2006-08-31 | 2007-08-30 | Oligomeric bis-phosphate flame retardants and compositions containing the same |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010502625A JP2010502625A (ja) | 2010-01-28 |
JP5508013B2 true JP5508013B2 (ja) | 2014-05-28 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2009526738A Active JP5508013B2 (ja) | 2006-08-31 | 2007-08-30 | オリゴマー状のビスホスフェート難燃剤およびこれを含有する組成物 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8119711B2 (ja) |
EP (1) | EP2089402B1 (ja) |
JP (1) | JP5508013B2 (ja) |
KR (1) | KR101416843B1 (ja) |
CN (1) | CN101511850B (ja) |
TW (1) | TWI400246B (ja) |
WO (1) | WO2008027536A1 (ja) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
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KR101701395B1 (ko) * | 2008-12-22 | 2017-02-01 | 아이씨엘-아이피 아메리카 아이엔씨. | 비스포스페이트를 정제하기 위한 수용성 용매 기반 정제 방법 |
EP2406307B1 (en) * | 2009-02-26 | 2012-12-12 | ICL-IP America Inc. | Styrenic polymer composition |
WO2010104689A1 (en) * | 2009-03-09 | 2010-09-16 | Icl-Ip America Inc. | Flame retarded polyolefin composition |
WO2011095552A1 (de) | 2010-02-05 | 2011-08-11 | Basf Se | Flammschutzmittel |
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EP2089402B1 (en) | 2015-08-05 |
KR20090045407A (ko) | 2009-05-07 |
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CN101511850A (zh) | 2009-08-19 |
TW200831522A (en) | 2008-08-01 |
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