JP4449751B2 - 変性ポリマーの製造方法及びそれにより製造された変性ポリマー - Google Patents
変性ポリマーの製造方法及びそれにより製造された変性ポリマー Download PDFInfo
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- 229920000642 polymer Polymers 0.000 title claims description 53
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 38
- -1 silane compound Chemical class 0.000 claims description 23
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910000077 silane Inorganic materials 0.000 claims description 5
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- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims 2
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- 239000004743 Polypropylene Substances 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 7
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- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
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- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
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- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- XOZUGNYVDXMRKW-AATRIKPKSA-N azodicarbonamide Chemical compound NC(=O)\N=N\C(N)=O XOZUGNYVDXMRKW-AATRIKPKSA-N 0.000 description 2
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- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- 229920002725 thermoplastic elastomer Polymers 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
- NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- 102100020870 La-related protein 6 Human genes 0.000 description 1
- 108050008265 La-related protein 6 Proteins 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920006465 Styrenic thermoplastic elastomer Polymers 0.000 description 1
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- RLDQYSHDFVSAPL-UHFFFAOYSA-L calcium;dithiocyanate Chemical group [Ca+2].[S-]C#N.[S-]C#N RLDQYSHDFVSAPL-UHFFFAOYSA-L 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
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- 238000010276 construction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
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- 125000004185 ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000005329 float glass Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 229920005555 halobutyl Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- ZQMHJBXHRFJKOT-UHFFFAOYSA-N methyl 2-[(1-methoxy-2-methyl-1-oxopropan-2-yl)diazenyl]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N=NC(C)(C)C(=O)OC ZQMHJBXHRFJKOT-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- 230000009257 reactivity Effects 0.000 description 1
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- 239000005060 rubber Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
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- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/42—Introducing metal atoms or metal-containing groups
-
- 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
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
- C08F279/04—Vinyl aromatic monomers and nitriles as the only monomers
-
- 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
- C08F8/00—Chemical modification by after-treatment
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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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)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
例えば特許文献1にはスチレン−エチレン−ブチレン−スチレン共重合体(SEBS)に不飽和カルボン酸もしくは酸無水物及びエポキシシランをグラフトさせる技術が提案されている。また特許文献2にはエポキシ基含有モノマーをポリプロピレンにグラフトし、ハイインパクトポリスチレン(HIPS)にガラス繊維とともに添加する技術が提案されている。
実施例及び比較例において使用した原料物質は以下の通りである。
SEBS:スチレン−エチレン−ブテン−スチレン共重合体〔旭化成(株)製、H1031〕
PP:ランダムポリプロピレン〔サンアロマー(株)製、サンアロマーPMC20M〕
ポリブテン:〔新日本石油化学(株)製、HV−100〕
ジ−t−ブチルパーオキサイド:〔日本油脂(株)製、パーブチルD〕
ジクミルパーオキサイド:〔日本油脂(株)製、パークミルD〕
OH−TEMPO:4−ヒドロキシ−2,2,6,6−テトラメチルピペリジニル−1−オキシル〔旭電化工業(株)製、LA7RD〕
3−トリメトキシシリルプロピルイソシアネート:〔信越化学(株)製〕
TDI:トリレンジイソシアネート〔三井武田ケミカル(株)製、コスモネート−100〕
SEBS350.0g、ジ−t−ブチルパーオキサイド7.40g及びOH−TEMPO10.5gを100℃に温度を設定した密閉型バンバリーに入れ15分間混合した。得られた混合物を、温度100℃に設定した密閉型バンバリー中で混練しながら5分間窒素置換した。混練しながら温度を175℃まで上昇させ30分間混錬した後、温度を150℃に下げ、3−トリメトキシシリルプロピルイソシアネート9.53gを系内に添加し、10分間混練した。得られたポリマーの一部をトルエンに溶解し、再沈殿操作によりポリマーを単離精製した。精製品を用いてIR分析ならびに1H−NMR分析を行って、ウレタン結合の存在及びアルコキシシリル基の導入を確認した。またその導入率は0.44mol%であった。
ポリプロピレン350.0g及びOH−TEMPO10.5gをドライブレンドし、145℃に温度設定した密閉型バンバリー中で混練しながら5分間窒素置換した。窒素フローした注入口からジ−t−ブチルパーオキサイド7.40gを注入し、混練しながら温度を175℃まで上昇させて30分間混練した後、温度を150℃に下げ、3−トリメトキシシリルプロピルイソシアネート9.53gを系内に添加し、10分間混練した。得られたポリマーの一部をトルエンに溶解し、再沈澱操作によりポリマーを単離精製した。精製品を用いてIR分析ならびに1H−NMR分析を行って、ウレタン結合の存在及びアルコキシシリル基の導入を確認した。またその導入率は0.48mol%であった。
変性ポリブテンの製造(実施例3)
300mLのフラスコにポリブテン40.3g(0.717mol)にジ−t−ブチルパーオキサイド5.27g(0.0211mol、2.95mol%)、OH−TEMPO6.18g(0.0358mol、5.0mol%)を加え、窒素雰囲気下、147℃で5時間攪拌した。次に、これにTDI0.549g(0.00315mol)を加えて90℃にて一晩攪拌した。1H−NMR及びIR分析によりウレタン結合及びイソシアネート基の導入を確認した。またその導入率は4.3mol%であった。
SEBS350.0g及び3−トリメトキシシリルプロピルイソシアネート9.53gを150℃に加熱した密閉型バンバリー中で10分間混練した。
PP350.0g及び3−トリメトキシシリルプロピルイソシアネート9.53gを150℃に加熱した密閉型バンバリー中で10分間混練した。
実施例1〜2及び比較例1〜2のポリマーの接着性を以下の方法で評価した。即ち、イソプロパノールで表面を払拭した各フロートガラス板(5×25×140mm)に帯状の各ポリマーをガラス板の中央部(5×15×100mm)に付着させ、前記ポリマーの付着厚が3mmになるようにプレス機にて加熱圧着させた(180℃×15分、4.9MPa)。
接着性試験
接着性評価
○…剥離しない
×…容易に剥離
Claims (7)
- 官能基(A)を有する2,2,6,6−テトラメチルピペリジニルオキシ(TEMPO)誘導体とラジカル開始剤をポリマーに添加して反応を行い、官能基(A)がグラフトされたポリマーを製造し、次いで必要に応じ添加剤を添加した後、官能基(A)と反応し得る官能基(B)を有する化合物を添加して反応させることを特徴とする変性ポリマーの製造方法。
- 官能基(A)がヒドロキシル基であるTEMPO誘導体を用いる請求項1に記載の製造方法。
- 官能基(B)を有する化合物がシラン化合物である請求項1又は2に記載の製造方法。
- 官能基(B)がイソシアネート基である請求項3に記載の製造方法。
- 請求項1〜4のいずれか1項に記載の製造方法により製造された変性ポリマー。
- 請求項5に記載の変性ポリマーを含むポリマー組成物。
- 変性ポリマーが請求項3で製造されたものである、ガラスとの接着性を有する請求項6に記載のポリマー組成物。
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JP2005003845A JP4449751B2 (ja) | 2005-01-11 | 2005-01-11 | 変性ポリマーの製造方法及びそれにより製造された変性ポリマー |
US11/813,492 US20080207845A1 (en) | 2005-01-11 | 2005-11-09 | Method For Producing Modified Polymer And Modified Polymer Produced By The Same |
KR1020077015367A KR20070099587A (ko) | 2005-01-11 | 2005-11-09 | 변성 폴리머의 제조 방법 및 그것에 의해 제조된 변성폴리머 |
PCT/JP2005/020984 WO2006075445A1 (ja) | 2005-01-11 | 2005-11-09 | 変性ポリマーの製造方法及びそれにより製造された変性ポリマー |
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JP4442688B2 (ja) * | 2007-12-13 | 2010-03-31 | 横浜ゴム株式会社 | 変性ブチルゴム組成物 |
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