JP5361043B2 - 結晶核剤およびそれを含有してなるポリオレフィン系樹脂組成物 - Google Patents
結晶核剤およびそれを含有してなるポリオレフィン系樹脂組成物 Download PDFInfo
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- JP5361043B2 JP5361043B2 JP2008243583A JP2008243583A JP5361043B2 JP 5361043 B2 JP5361043 B2 JP 5361043B2 JP 2008243583 A JP2008243583 A JP 2008243583A JP 2008243583 A JP2008243583 A JP 2008243583A JP 5361043 B2 JP5361043 B2 JP 5361043B2
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 238000004806 packaging method and process Methods 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
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002589 poly(vinylethylene) polymer Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000377 silicon dioxide 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
- 235000011049 sodium adipate Nutrition 0.000 description 1
- 239000001601 sodium adipate Substances 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
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- 150000003672 ureas Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
(式中、Rは分岐を有してもよい炭素原子数1〜5のアルキレン基であり、環Aおよび環Bは、各々独立して、置換基を有していてもよい炭素原子数3〜12のシクロアルキル基、または置換基を有していてもよい炭素原子数6〜20のアリール基を表し、X1〜X4は、各々独立して、ハロゲン原子、置換されていてもよく分岐を有してもよい炭素原子数1〜4のアルキル基、および置換されていてもよく分岐を有してもよい炭素原子数1〜4のアルコキシ基よりなる群から選択されるものを表し、p、q、rおよびsは各々独立して、0〜3の整数(ただし、pおよびsは0ではない)を表す)で表されることを特徴とするものである。
本発明の結晶核剤は、下記一般式(1)、
(式中、Rは分岐を有してもよい炭素原子数1〜5のアルキレン基であり、環Aおよび環Bは、各々独立して、置換基を有していてもよい炭素原子数3〜12のシクロアルキル基、または置換基を有していてもよい炭素原子数6〜20のアリール基を表し、X1〜X4は、各々独立して、ハロゲン原子、置換されていてもよく分岐を有してもよい炭素原子数1〜4のアルキル基、および置換されていてもよく分岐を有してもよい炭素原子数1〜4のアルコキシ基よりなる群から選択されるものを表し、p、q、rおよびsは各々独立して、0〜3の整数(ただし、pおよびsは0ではない)を表す)で表される構造からなるものである。
本発明に係るポリオレフィン系樹脂としては、ポリエチレン樹脂、ポリプロピレン樹脂およびポリブテン樹脂等が挙げられ、より具体的には、高密度ポリエチレン、中密度ポリエチレン、直鎖状ポリエチレン、シクロオレフィンポリマー、エチレンコポリマー、プロピレンホモポリマー、プロピレンコポリマー、ブテンホモポリマー、ブテンコポリマー、メチルペンテンホモポリマー、メチルペンテンコポリマー等が挙げられる。
窒素雰囲気下、4,4’−メチレンビス(2,6−ジエチルアニリン)6.2g(0.02mol)、ジメチルアセトアミド50g、ピリジン3.2g(0.04mol)、o−トルイル酢酸6.0g(0.04mol)およびトリフェニルフォスフェイト12.4g(0.04mol)を80℃で4時間撹拌して反応させた。反応終了後、蒸留水を加えてさらに80℃で30分間撹拌し、室温下で放冷して冷却した。冷却後、生じた析出物を減圧濾過によって濾別し、残渣をイソプロパノールで再沈殿させた。再沈殿した析出物を濾別して、白色固体10.7g(収率:93%)を得た。該白色固体をFT−IRで分析した結果、目的物の化合物No.1と同定した。これらの分析結果について下記に示す。
741、1520、1655、2963、3252
上記合成例1において、o−トルイル酢酸6.0g(0.04mol)をm−トルイル酢酸6.0g(0.04mol)に変更した以外は、上記合成例1と同様に実施して、化合物No.2を9.7g(収率85%)合成した。
上記合成例1において、o−トルイル酢酸6.0g(0.04mol)をp−トルイル酢酸6.0g(0.04mol)に変更した以外は、上記合成例1と同様に実施して、化合物No.3を10.3g(収率:90%)合成した。
上記合成例1において、o−トルイル酢酸6.0g(0.04mol)を1−クロロ−2−ベンゼンエタン酸5.4g(0.04mol)に変更した以外は、上記合成例1と同様に実施して、化合物No.7を9.9g(収率:80%)合成した。
上記合成例1において、4,4’−メチレンビス(2,6−ジエチルアニリン)6.21g(0.02mol)を、2,2−エチレンビスジアニリン4.2g(0.02mol)に変更した以外は、上記合成例1と同様に実施して、化合物No.9を8.1g(収率:90%)合成した。
230℃、21.2Nでのメルトフローレートが10g/10分であるエチレン/プロピレンランダム共重合体(エチレン含有量;3質量%)100質量部に対し、フェノール系抗酸化剤;テトラキス[メチレン−3−(3’,5’−ジ第三ブチル−4’−ヒドロキシフェニル)プロピオネート]メタン0.1質量部、リン系抗酸化剤:トリス(2,4−ジ第三ブチルフェニル)ホスファイト0.1質量部、ステアリン酸カルシウム0.05質量部、および表1記載の結晶核剤を、ヘンシェルミキサー(FM200;三井鉱山株式会社製)で1000rpm、1分間混合し、単軸押出機(OEX3024;株式会社ディ・ディ・エム製)で、240℃、30rpmのスクリュー速度の加工条件で押出加工してペレットを製造した。得られたペレットについて、90℃で3時間乾燥後、下記の評価を実施した。
前記の得られたペレットを、射出成型機(EC100−2A;東芝機械株式会社製)にて、230℃の射出温度および50〜60MPaの射出圧力で金型に40秒間充填し、40℃の金型内で20秒間冷却後、金型からシートを取り出す条件で射出成形を行って、一辺が60mm四方の正方形で厚みが1mmのシートを得た。該シートは射出成形後ただちに槽内温度が23℃である恒温槽で48時間以上静置した後、ヘイズ・ガードII〔株式会社東洋精機製作所製〕にて、試験片の透明性(HAZE)を求めた。この結果を下記表1に示す。
得られたペレットを、示差走査熱量測定機(ダイアモンド;パーキンエルマー社製)にて、50℃/minの速度で300℃まで昇温し、10分間保持後−10℃/minの速度で100℃まで冷却して得られたチャートにおいて、吸熱のピークトップを結晶化温度とした。これらの結果について下記の表1に示す。
Claims (5)
- 前記一般式(2)中のX1およびX4がベンゼン環のオルト位にある請求項2記載の結晶核剤。
- 前記一般式(2)中のpおよびsが1を表し,qおよびrが2である請求項2または3記載の結晶核剤。
- ポリオレフィン系樹脂100質量部に対して、請求項1〜4のうちいずれか一項に記載の結晶核剤0.01〜1.0質量部を含有することを特徴とするポリオレフィン系樹脂組成物。
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PCT/JP2009/064620 WO2010024191A1 (ja) | 2008-08-28 | 2009-08-21 | ポリオレフィン系樹脂組成物 |
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