JP2010196033A - 食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物 - Google Patents
食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物 Download PDFInfo
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- JP2010196033A JP2010196033A JP2009254467A JP2009254467A JP2010196033A JP 2010196033 A JP2010196033 A JP 2010196033A JP 2009254467 A JP2009254467 A JP 2009254467A JP 2009254467 A JP2009254467 A JP 2009254467A JP 2010196033 A JP2010196033 A JP 2010196033A
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- 239000011342 resin composition Substances 0.000 title claims abstract description 45
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- 235000013305 food Nutrition 0.000 title claims abstract description 31
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 47
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- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
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- 239000006078 metal deactivator Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000012968 metallocene catalyst Substances 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 239000004843 novolac epoxy resin Substances 0.000 description 1
- CYCBIVGDSMISKD-UHFFFAOYSA-N o-tridecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanethioate Chemical compound CCCCCCCCCCCCCOC(=S)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 CYCBIVGDSMISKD-UHFFFAOYSA-N 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl 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])=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])[H] 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-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
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 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
- 235000014786 phosphorus Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000011158 quantitative evaluation Methods 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- GDESWOTWNNGOMW-UHFFFAOYSA-N resorcinol monobenzoate Chemical compound OC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 GDESWOTWNNGOMW-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- KYKFCSHPTAVNJD-UHFFFAOYSA-L sodium adipate Chemical compound [Na+].[Na+].[O-]C(=O)CCCCC([O-])=O KYKFCSHPTAVNJD-UHFFFAOYSA-L 0.000 description 1
- 239000001601 sodium adipate Substances 0.000 description 1
- 235000011049 sodium adipate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- ZHROMWXOTYBIMF-UHFFFAOYSA-M sodium;1,3,7,9-tetratert-butyl-11-oxido-5h-benzo[d][1,3,2]benzodioxaphosphocine 11-oxide Chemical compound [Na+].C1C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP([O-])(=O)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C ZHROMWXOTYBIMF-UHFFFAOYSA-M 0.000 description 1
- SNAQARSCIHDMGI-UHFFFAOYSA-M sodium;bis(4-tert-butylphenyl) phosphate Chemical compound [Na+].C1=CC(C(C)(C)C)=CC=C1OP([O-])(=O)OC1=CC=C(C(C)(C)C)C=C1 SNAQARSCIHDMGI-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- WUPCFMITFBVJMS-UHFFFAOYSA-N tetrakis(1,2,2,6,6-pentamethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)CC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 WUPCFMITFBVJMS-UHFFFAOYSA-N 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-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
- KOWVWXQNQNCRRS-UHFFFAOYSA-N tris(2,4-dimethylphenyl) phosphate Chemical compound CC1=CC(C)=CC=C1OP(=O)(OC=1C(=CC(C)=CC=1)C)OC1=CC=C(C)C=C1C KOWVWXQNQNCRRS-UHFFFAOYSA-N 0.000 description 1
- LTXMJHWSYUANCC-UHFFFAOYSA-N tris(2,4-ditert-butyl-5-methylphenyl) phosphite Chemical compound C1=C(C(C)(C)C)C(C)=CC(OP(OC=2C(=CC(=C(C)C=2)C(C)(C)C)C(C)(C)C)OC=2C(=CC(=C(C)C=2)C(C)(C)C)C(C)(C)C)=C1C(C)(C)C LTXMJHWSYUANCC-UHFFFAOYSA-N 0.000 description 1
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- SGKKYCDALBXNCG-UHFFFAOYSA-N tris[2-tert-butyl-4-(3-tert-butyl-4-hydroxy-5-methylphenyl)sulfanyl-5-methylphenyl] phosphite Chemical compound CC(C)(C)C1=C(O)C(C)=CC(SC=2C(=CC(OP(OC=3C(=CC(SC=4C=C(C(O)=C(C)C=4)C(C)(C)C)=C(C)C=3)C(C)(C)C)OC=3C(=CC(SC=4C=C(C(O)=C(C)C=4)C(C)(C)C)=C(C)C=3)C(C)(C)C)=C(C=2)C(C)(C)C)C)=C1 SGKKYCDALBXNCG-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
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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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
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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
- C08K5/16—Nitrogen-containing compounds
- C08K5/20—Carboxylic acid amides
-
- 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
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5455—Silicon-containing compounds containing nitrogen containing at least one group
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Rigid Pipes And Flexible Pipes (AREA)
Abstract
【解決手段】下記一般式(I)、
(式中、R1及びR2は、各々独立して、水素原子等を表し、Tは分岐および/またはシクロアルキル基を有してもよい炭素原子数1〜30のアルキル基等を表す)で表されるフェノール系酸化防止剤を有機アルミニウム化合物でマスキング処理したものを、オレフィン系モノマーの重合前又は重合中に、触媒系又は重合系に添加して重合したポリオレフィン系樹脂を含有する食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物であって、前記ポリオレフィン系モノマー100質量部に対し、前記一般式(I)で表されるフェノール系酸化防止剤を0.001〜0.5質量部添加してなる食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物である。
【選択図】なし
Description
(式中、R1及びR2は、各々独立して、水素原子、分岐を有してもよい炭素原子数1〜5のアルキル基、又は炭素原子数7〜9のフェニルアルキル基を表し、Tは分岐および/またはシクロアルキル基を有してもよい炭素原子数1〜30のアルキル基または炭素原子数2〜30のアルケニル基、置換基を有してもよい炭素原子数3〜12のシクロアルキル基、置換基を有してもよい炭素原子数6〜18のアリール基を表す)で表されるフェノール系酸化防止剤を有機アルミニウム化合物でマスキング処理したものを、オレフィン系モノマーの重合前又は重合中に、触媒系又は重合系に添加して重合したポリオレフィン系樹脂を含有する食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物であって、前記オレフィン系モノマー100質量部に対し、前記一般式(I)で表されるフェノール系酸化防止剤を0.001〜0.5質量部添加してなることを特徴とするものである。
本発明に用いられるフェノール系酸化防止剤とは、下記一般式(I)で表される化合物であり、オレフィン系モノマー100質量部に対して、0.001〜0.5質量部、より好ましくは0.005〜0.3質量部となるように用いられる。
(式中、R1及びR2は、各々独立して、水素原子、分岐を有してもよい炭素原子数1〜5のアルキル基、又は炭素原子数7〜9のフェニルアルキル基を表し、Tは分岐および/またはシクロアルキル基を有してもよい炭素原子数1〜30のアルキル基または炭素原子数2〜30のアルケニル基、置換基を有してもよい炭素原子数3〜12のシクロアルキル基、置換基を有してもよい炭素原子数6〜18のアリール基を表す)
下記の手順([1]触媒スラリーの調製、[2]安定剤溶液の調製、[3]オレフィン系モノマーの重合)に従いポリオレフィン系樹脂組成物を得た。
無水塩化マグネシウム4.76g(50mmol)、デカン25mL及び2−エチルへキシルアルコール23.4mL(150mmol)を加えて、130℃で2時間加熱反応を行い均一溶液とした後、さらに無水フタル酸1.11g(7.5mmol)を添加し、130℃を維持しながら1時間撹拌して、無水フタル酸を該均一溶液に溶解させた。次に、均一溶液を室温に冷却し、−20℃に保持された四塩化チタン200mL(1.8mol)中に1時間にわたって全量滴下装入した。装入終了後、4時間かけて110℃まで昇温した。110℃に到達後、ジイソブチルフタレート2.68mL(12.5mmol)を加え、110℃を維持しながら2時間撹拌して反応させた。反応終了後、熱時ろ過にて残渣を採取し、該残渣を200mLの四塩化チタンにて再懸濁させた後、再び110℃まで加熱して2時間反応させた。反応終了後、再び熱時ろ過で残渣を採取し、110℃のデカン及びヘキサンにて、洗液中に遊離しているチタン化合物が検出されなくなるまで充分に洗浄して固体チタン触媒成分を得た。この固体チタン触媒成分の一部をサンプリングして乾燥し、触媒組成を分析したところ、チタン3.1質量%、塩素56.0質量%、マグネシウム17.0質量%及びイソブチルフタレート20.9質量%であった。以上の製造方法にて合成された固体チタン触媒成分に、ヘプタンスラリーとして5mg/mLとなるようにヘプタンを加えて触媒スラリーを調製した。
窒素置換したフラスコに3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)−N−オクタデシルプロピオンアミド(1.03g,1.94mmol)及び、乾燥ヘプタン65.5mLを加えた。撹拌しながら、トリエチルアルミニウム/ヘプタン溶液3.0mL(1mol/L)を滴下し、フェノキシド溶液を調製した。
窒素置換したオートクレーブに、乾燥ヘプタン600mL及びトリエチルアルミニウム/ヘプタン溶液2.2mL(1mol/L)を加えた。さらに、上記[2]で調製したフェノキシド溶液6.5mL、乾燥ヘプタン100mLにジシクロペンチルジメトキシシラン1.2g(5.3mmol)を撹拌して溶解させたヘプタン溶液4.1mL、及び上記[1]で調製した触媒スラリー4.0mLを順次加えた。オートクレーブ内をプロピレン雰囲気に置換し、水素(0.34L;標準状態換算)を入れ、プロピレン圧0.098MPa(G)、50℃で5分間プレ重合(600rpm)を行った。その後、プロピレン圧0.59MPa、70℃で1時間重合反応を行った。気体をパージ後、反応液にエタノール5mLを加え5分間撹拌して重合反応を停止させた後、減圧脱溶媒を行い、次いで、真空中、40℃で10時間乾燥することにより、ポリオレフィン系樹脂組成物を得た。
上記実施例1の[3]重合において、フェノキシド溶液6.5mLを、下記のホスファイト溶液6.7mLに代えた以外は、実施例1の[3]の重合と同様に実施して、ポリオレフィン系樹脂組成物を得た。
窒素置換したフラスコに、トリス(2,4−ジ第三ブチルフェニル)ホスファイト0.9g(1.4mmol)及び乾燥ヘプタン30mLを加えて、撹拌し、ホスファイト溶液を調製した。
上記実施例1の[3]重合において、フェノキシド溶液6.5mLを用いなかった以外は、実施例1の[3]と同様に実施して、ポリオレフィン系樹脂を重合した。次に、3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)−N−オクタデシルプロピオンアミドが500ppmになるように、ポリオレフィン系樹脂と混合し、単軸押出機(装置:株式会社東洋精機製作所製プラストミルμ、押出温度:230℃、スクリュー回転速度:50rpm)で造粒してペレットを得た。
上記の得られたポリオレフィン系樹脂組成物又はペレットを、ドライアイスで凍結させてからローラーミル(HEIKO SAMPLE MILL T1−500ET;HEIKO 製作所製)にて一時間粉砕した。粉砕されたポリオレフィン系樹脂5〜10gにクロロホルム100mLを加え、スチームバス上で加熱還流下4時間抽出した。抽出後、ろ別して、ろ液は回収し、ろ過残留物は、再度新しいクロロホルム100mLを加えて、スチームバス上で加熱還流下4時間抽出した。抽出後、ろ別し、ろ液のクロロホルム溶媒と、先の抽出で得られたろ液のクロロホルム溶媒を併せて濃縮し、さらに、アセトン100mLを加えて、スチームバス上で1時間加熱還流し、室温まで冷却後、ろ別して、ろ液を濃縮し、クロロホルムで10mLに秤量した。
2)比較化合物1:トリス(2,4−ジ第三ブチルフェニル)ホスファイト
3)重合時:オレフィン系モノマーの重合時に安定剤を添加
4)造粒時:オレフィン系モノマーの重合後、安定剤を添加して混合し、押出機を用いて230℃の押出温度で造粒した。
実施例1で得られたポリオレフィン系樹脂組成物10mgを採取し、微量全窒素分析装置(TN−110;三菱化学株式会社製)を用いて、全窒素含有量を測定した。検量線は、ピリジンをキシレンに溶解したものを用いて作成した。
Claims (6)
- 下記一般式(I)、
(式中、R1及びR2は、各々独立して、水素原子、分岐を有してもよい炭素原子数1〜5のアルキル基、又は炭素原子数7〜9のフェニルアルキル基を表し、Tは分岐および/またはシクロアルキル基を有してもよい炭素原子数1〜30のアルキル基または炭素原子数2〜30のアルケニル基、置換基を有してもよい炭素原子数3〜12のシクロアルキル基、置換基を有してもよい炭素原子数6〜18のアリール基を表す)で表されるフェノール系酸化防止剤を有機アルミニウム化合物でマスキング処理したものを、オレフィン系モノマーの重合前又は重合中に、触媒系又は重合系に添加して重合したポリオレフィン系樹脂を含有する食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物であって、前記オレフィン系モノマー100質量部に対し、前記一般式(I)で表されるフェノール系酸化防止剤を0.001〜0.5質量部添加してなることを特徴とする食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物。 - 前記一般式(I)中のTが、分岐を有してもよい炭素原子数12〜24のアルキル基である請求項1記載の食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物。
- 前記有機アルミニウム化合物が、トリアルキルアルミニウムである請求項1または2記載の食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物。
- 前記オレフィン系モノマーの重合触媒が、遷移金属触媒である請求項1〜3のうちいずれか一項記載の食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物。
- 前記オレフィン系モノマーの重合触媒が、チーグラー・ナッタ触媒である請求項1〜4のうちいずれか一項記載の食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物。
- 樹脂に配合された前記フェノール系酸化防止剤の量に対して、クロロホルムを溶媒として環流抽出された前記フェノール系酸化防止剤の割合が20質量%以下である請求項1〜5のうちいずれか一項記載の食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物。
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CN200980155677XA CN102300919A (zh) | 2009-01-28 | 2009-11-13 | 食品/医疗/自来水管用途的聚烯烃系树脂组合物 |
US13/146,570 US20110288216A1 (en) | 2009-01-28 | 2009-11-13 | Polyolefin-based resin composition for food, medical, and municipal water pipe applications |
KR1020117019864A KR20110107866A (ko) | 2009-01-28 | 2009-11-13 | 식품·의료·수도용 파이프 용도의 폴리올레핀계 수지 조성물 |
PCT/JP2009/069328 WO2010087064A1 (ja) | 2009-01-28 | 2009-11-13 | 食品・医療・水道用パイプ用途のポリオレフィン系樹脂組成物 |
EP09839253A EP2392616A4 (en) | 2009-01-28 | 2009-11-13 | POLYOLEFIN RESIN COMPOSITION FOR FOOD, MEDICAL AND CITY WATER POWDER APPLICATIONS |
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JP2012057101A (ja) * | 2010-09-10 | 2012-03-22 | Adeka Corp | 安定化ポリマーの製造方法 |
WO2013140905A1 (ja) * | 2012-03-23 | 2013-09-26 | 株式会社Adeka | 家電材料用及び自動車内装材料用オレフィン樹脂組成物の製造方法 |
JP2016173328A (ja) * | 2015-03-17 | 2016-09-29 | 日本ポリプロ株式会社 | ポリオレフィン中に含まれる添加剤の定量分析方法 |
JP2017524877A (ja) * | 2014-06-11 | 2017-08-31 | フイナ・テクノロジー・インコーポレーテツドFina Technology, Incorporated | 耐塩素性ポリエチレン化合物およびそれから製造される製品 |
JP2019536017A (ja) * | 2017-09-12 | 2019-12-12 | エルジー・ケム・リミテッド | 高分子量酸化防止剤の定量分析方法 |
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WO2011027793A1 (ja) * | 2009-09-04 | 2011-03-10 | 株式会社Adeka | フェノール系酸化防止剤の再生方法、オレフィン重合体の製造方法、ポリオレフィンパウダー、及び繊維 |
EP2966095B1 (en) * | 2011-03-02 | 2017-05-03 | Adeka Corporation | Process of producing resin composition for coating members |
JP6433726B2 (ja) * | 2014-08-27 | 2018-12-05 | 株式会社Adeka | 熱安定剤組成物およびこれを用いた合成樹脂組成物 |
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WO2010087064A1 (ja) | 2010-08-05 |
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