JP2017128698A - 帯電防止性熱可塑性樹脂組成物およびそれを成形してなる成形体 - Google Patents
帯電防止性熱可塑性樹脂組成物およびそれを成形してなる成形体 Download PDFInfo
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- JP2017128698A JP2017128698A JP2016010838A JP2016010838A JP2017128698A JP 2017128698 A JP2017128698 A JP 2017128698A JP 2016010838 A JP2016010838 A JP 2016010838A JP 2016010838 A JP2016010838 A JP 2016010838A JP 2017128698 A JP2017128698 A JP 2017128698A
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- 229920002961 polybutylene succinate Polymers 0.000 description 1
- 239000004631 polybutylene succinate Substances 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
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- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
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- 229920000915 polyvinyl chloride Polymers 0.000 description 1
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- 235000011164 potassium chloride Nutrition 0.000 description 1
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- RBTVSNLYYIMMKS-UHFFFAOYSA-N tert-butyl 3-aminoazetidine-1-carboxylate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)N1CC(N)C1 RBTVSNLYYIMMKS-UHFFFAOYSA-N 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
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-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
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- 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
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- 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
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- DECPGQLXYYCNEZ-UHFFFAOYSA-N tris(6-methylheptyl) phosphite Chemical compound CC(C)CCCCCOP(OCCCCCC(C)C)OCCCCCC(C)C DECPGQLXYYCNEZ-UHFFFAOYSA-N 0.000 description 1
- JZNDMMGBXUYFNQ-UHFFFAOYSA-N tris(dodecylsulfanyl)phosphane Chemical compound CCCCCCCCCCCCSP(SCCCCCCCCCCCC)SCCCCCCCCCCCC JZNDMMGBXUYFNQ-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
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
前記高分子化合物(A)が、ジオール、脂肪族ジカルボン酸、芳香族ジカルボン酸、下記一般式(1)、
で表される基を一つ以上有し、両末端に水酸基を有する化合物(C)、および、反応性官能基を有する化合物(D)が、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有することを特徴とするものである。
で表される基を一つ以上有し、両末端に水酸基を有する化合物(C)、および、反応性官能基を有する化合物(D)とが、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有している。
本発明の樹脂組成物において利用可能な樹脂は、熱可塑性樹脂であれば制限はないが、帯電防止性能の持続性と成形性の観点から、特に、ポリオレフィン系樹脂、スチレン系樹脂、ポリエステル系樹脂、ポリエーテル系樹脂、ポリカーボネート系樹脂、ポリアミド系樹脂、含ハロゲン樹脂が好ましい。
高分子化合物(A)は、樹脂組成物に帯電防止性を付与するために配合される。本発明で用いる高分子化合物(A)は、ジオールと、脂肪族ジカルボン酸と、芳香族ジカルボン酸と、下記一般式(1)で表される基を一つ以上有し、両末端に水酸基を有する化合物(C)と、反応性官能基を有する化合物(D)とが、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有している。
化合物(C)は、親水性を有する化合物が好ましく、上記一般式(1)で示される基を有するポリエーテルがより好ましく、下記一般式(2)で表されるポリエチレングリコールが特に好ましい。
本発明において反応性官能基を有する化合物(D)は、カルボキシル基とエステル結合を介して結合するもの、またはアミド結合を介して結合できるものであればよく、ポリエステル(E)、および化合物(C)と、エステル結合またはアミド結合を介して結合しうるもの、あるいは、ポリエステル(E)から構成されたブロック、および化合物(C)から構成されたブロックがエステル結合を介して繰り返し交互に結合してなる両末端にカルボキシル基を有するブロックポリマー(G)と、エステル結合またはアミド結合を介して結合し得るものであればよい。かかる官能基としては、エポキシ基、水酸基、アミノ基等が挙げられる。
上述のとおり、本発明の樹脂組成物においては、高分子化合物(A)は、帯電防止性の観点から、ジオール、脂肪族ジカルボン酸および芳香族ジカルボン酸から構成されるポリエステル(E)、化合物(C)、および反応性官能基を有する化合物(D)が、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有することが好ましい。
本発明に係る両末端にカルボキシル基を有する構造のブロックポリマー(G)は、ポリエステル(E)から構成されたブロックと、化合物(C)から構成されたブロックとを有し、これらのブロックが、カルボキシル基と水酸基とにより形成されたエステル結合を介して繰り返し交互に結合してなる構造を有する。かかるブロックポリマー(G)の一例を挙げると、例えば、下記一般式(3)で表される構造を有するものが挙げられる。
アミン系酸化防止剤(B)はアミン構造を有し、熱可塑性樹脂に耐熱性を付与する化合物であれば、特に制限なく、高分子化合物(A)と一緒に熱可塑性樹脂に添加することができる。
(1)イミダゾリニウムカチオン
炭素原子数5〜15のものが挙げられ、例えば、1,2,3,4−テトラメチルイミダゾリニウム、1,3−ジメチルイミダゾリニウム;
(2)イミダゾリウムカチオン
炭素原子数5〜15のものが挙げられ、例えば、1,3−ジメチルイミダゾリウム、1−エチル−3−メチルイミダゾリウム;
(3)テトラヒドロピリミジニウムカチオン
炭素原子数6〜15のものが挙げられ、例えば、1,3−ジメチル−1,4,5,6−テトラヒドロピリミジニウム、1,2,3,4−テトラメチル−1,4,5,6−テトラヒドロピリミジニウム;
(4)ジヒドロピリミジニウムカチオン
炭素原子数6〜20のものが挙げられ、例えば、1,3−ジメチル−1,4−ジヒドロピリミジニウム、1,3−ジメチル−1,6−ジヒドロピリミジニウム、8−メチル−1,8−ジアザビシクロ[5,4,0]−7,9−ウンデカジエニウム、8−メチル−1,8−ジアザビシクロ[5,4,0]−7,10−ウンデカジエニウム。
(1)イミダゾリニウム骨格を有するグアニジニウムカチオン
炭素原子数8〜15のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチルイミダゾリニウム、2−ジエチルアミノ−1,3,4−トリメチルイミダゾリニウム;
(2)イミダゾリウム骨格を有するグアニジニウムカチオン
炭素原子数8〜15のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチルイミダゾリウム、2−ジエチルアミノ−1,3,4−トリメチルイミダゾリウム;
(3)テトラヒドロピリミジニウム骨格を有するグアニジニウムカチオン
炭素原子数10〜20のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチル−1,4,5,6−テトラヒドロピリミジニウム、2−ジエチルアミノ−1,3−ジメチル−4−エチル−1,4,5,6−テトラヒドロピリミジニウム;
(4)ジヒドロピリミジニウム骨格を有するグアニジニウムカチオン
炭素原子数10〜20のものが挙げられ、例えば、2−ジメチルアミノ−1,3,4−トリメチル−1,4−ジヒドロピリミジニウム、2−ジメチルアミノ−1,3,4−トリメチル−1,6−ジヒドロピリミジニウム、2−ジエチルアミノ−1,3−ジメチル−4−エチル−1,4−ジヒドロピリミジニウム、2−ジエチルアミノ−1,3−ジメチル−4−エチル−1,6−ジヒドロピリミジニウム。
ここで、一般式(4)中、x1およびx2はそれぞれ下記式、
0≦x2/x1<10,2≦x1+x2≦20
で表される条件を満たす数を表し、pは0または正の数を表す。
ここで、一般式(5)中、Aq−は、q価のアニオンを表し、pは0または正の数を表す。また、ハイドロタルサイト類における炭酸アニオンは、一部を他のアニオンで置換したものでもよい。
本発明の成形体は、本発明の樹脂組成物が成形されてなるものである。本発明の樹脂組成物を成形することにより、優れた帯電防止性と高い耐熱性を有する成形体を製造することができる。成形方法は特に限定されるものではなく、押出加工、カレンダー加工、射出成形、ロール、圧縮成形、ブロー成形、回転成形等が挙げられ、樹脂板、シート、フィルム、ボトル、繊維、異形品等の種々の形状の成形体を製造することができる。
下記の製造例に従い、高分子化合物(A)を製造した。また、下記の製造例において数平均分子量は、下記の方法で測定した。
数平均分子量(以下、「Mn」と称する)は、ゲルパーミエーションクロマトグラフィー(GPC)法によって測定した。Mnの測定条件は以下の通りである。
装置 :日本分光株式会社製GPC装置
溶媒 :テトラヒドロフラン
基準物質 :ポリスチレン
検出器 :示差屈折計(RI検出器)
カラム固定相 :昭和電工株式会社製Shodex KF−804L
カラム温度 :40℃
サンプル濃度 :1mg/1mL
流量 :0.8mL/min.
注入量 :100μL
セパラブルフラスコに、ジオールとして、1,4−シクロヘキサンジメタノールを656g(4.55モル)、脂肪族ジカルボン酸として、アジピン酸を708g(4.85モル)、芳香族ジカルボン酸として、無水フタル酸を0.7g(4.73×10−3モル)、酸化防止剤(テトラキス[3−(3,5−ジ第三ブチル−4−ヒドロキシフェニル)プロピオニルオキシメチル]メタン;株式会社ADEKA製商品名「アデカスタブAO−60」)を0.7g仕込み、160℃から210℃まで徐々に昇温しながら常圧で5時間、その後210℃、減圧下で3時間重合してポリエステル(E)−1を得た。ポリエステル(E)−1の酸価は28、数平均分子量Mnはポリスチレン換算で5,400であった。
セパラブルフラスコに、ジオールとして、1,4−ビス(β−ヒドロキシエトキシ)ベンゼンを370g(1.87モル)、脂肪族ジカルボン酸として、アジピン酸を289g(1.98モル)、芳香族ジカルボン酸として、イソフタル酸を8g(0.05モル)、酸化防止剤(アデカスタブAO−60)を0.5g仕込み、180℃から220℃まで徐々に昇温しながら常圧で5時間重合した。その後、テトライソプロポキシチタネートを0.5g仕込み、220℃、減圧下で5時間重合して、ポリエステル(E)−2を得た。ポリエステル(E)−2の酸価は56、数平均分子量Mnは、ポリスチレン換算で4,900であった。
セパラブルフラスコに、ジオールとして、ビスフェノールAのエチレンオキサイド付加物を591g、脂肪族ジカルボン酸として、セバシン酸を235g(1.16モル)、芳香族ジカルボン酸として、イソフタル酸を8g(0.05モル)、一般式(1)で表される基を一つ以上有し両末端に水酸基を有する化合物(C)として、数平均分子量2,000のポリエチレングリコール(C)−2を300g、酸化防止剤(アデカスタブAO−60)を0.8g仕込み、180℃から220℃まで徐々に昇温しながら常圧で5時間重合した。その後、テトライソプロポキシチタネートを0.6g仕込み、220℃、減圧下で7時間重合して、両末端にカルボキシルを有するブロックポリマー(G)−3を得た。このブロックポリマー(G)−3の酸価は10、数平均分子量Mnはポリスチレン換算で10,100であった。
上記の製造方法で得られた高分子化合物(A)−1〜(A)−3を用いて、下記の方法で試験片を作製し、評価を実施した。
フェノール系酸化防止剤(株式会社ADEKA製商品名「アデカスタブAO−60」)0.1質量部、リン系酸化防止剤(株式会社ADEKA製商品名「アデカスタブ2112」)0.1質量部、ステアリン酸カルシウム0.05質量、および、下記の表1〜5に示す配合量に基づいてブレンドした樹脂組成物を、株式会社池貝製 二軸押出機(製品名:PCM30,60メッシュのスクリーン入り)を用いて、230℃、9kg/時間の条件で造粒し、ペレットを得た。得られたペレットを、日精樹脂工業株式会社製 横型射出成形機(製品名 NEX80)を用い、樹脂温度230℃、金型温度50℃の加工条件で成形し、試験片(100mm×100mm×3mm)を作製した。これらの試験片を用いて、下記の条件に従い、表面固有抵抗値の測定と熱安定性を評価した。
熱可塑性樹脂1(ポリプロピレン):ホモポリプロピレン(メルトフローレート(ISO1133 230℃×2.16kg)=8g/10min)
熱可塑性樹脂2(ポリエチレン):高密度ポリエチレン(メルトフローレート=7g/10min)日本ポリエチレン株式会社製商品名「ノバテックHD HJ560」
熱可塑性樹脂3(スチレン系樹脂):耐衝撃性ポリスチレン(メルトフローレート=2.7g/10min)東洋スチレン株式会社製商品名「E640N」
化合物1:N,N−ジステアリルヒドロキシルアミン
比較化合物1:ポリエーテルエステルアミド型帯電防止剤,BASF社製商品名「イルガスタットP−18」
比較化合物2:ポリエーテルエステルアミド型帯電防止剤、BASF社製商品名「イルガスタットP−20」
アルカリ金属塩(F)−1:ドデシルベンゼンスルホン酸ナトリウム
アルカリ金属塩(F)−2:p−トルエンスルホン酸リチウム
得られた試験片(100mm×100mm×3mm)を、成形加工後直ちに、100℃のオーブン内に静置し、成形加工の24時間後および1000時間後に、25℃、湿度60%RHの条件下に1日保存し、同雰囲気下で、アドバンテスト社製のR8340抵抗計を用いて、印加電圧500V、印加時間1分の条件で、表面固有抵抗値(Ω/□)を測定した。測定は5点について行い、その平均値を求めた。これらの結果についてそれぞれ下記表1〜5に示す。
得られた試験片(100mm×100mm×3mm)を、スガ試験株式会社製分光測色計SC−Pを用いてYI(Yellowness Index)を測定した。次に、試験片を100℃のオーブンに入れ静置した。1000時間経過後、試験片をオーブンから取り出してYIを測定し、オーブンに入れる前の試験片のYIとの差(ΔYI)を算出した。これらの試験結果について、それぞれ下記表1〜5に示す。なお、ΔYIは、小さいほど変色が少なく熱安定に優れることを表す。
Claims (11)
- 前記アミン系酸化防止剤が、ヒドロキシルアミン化合物である請求項1記載の帯電防止性熱可塑性樹脂組成物。
- 前記高分子化合物(A)が、ジオール、脂肪族ジカルボン酸、および芳香族ジカルボン酸から構成されるポリエステル(E)と、前記化合物(C)と、前記化合物(D)とが、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる請求項1または2記載の帯電防止性熱可塑性樹脂組成物。
- 前記高分子化合物(A)が、前記ポリエステル(E)から構成されたブロックおよび前記化合物(C)から構成されたブロックがエステル結合を介して繰り返し交互に結合してなる両末端にカルボキシル基を有するブロックポリマー(G)と、前記化合物(D)とが、エステル結合を介して、または、エステル結合およびアミド結合を介して結合してなる構造を有する請求項3記載の帯電防止性熱可塑性樹脂組成物。
- 前記ポリエステル(E)から構成されたブロックの数平均分子量がポリスチレン換算で800〜8,000であり、前記化合物(C)から構成されたブロックの数平均分子量がポリスチレン換算で400〜6,000であり、かつ、前記ブロックポリマー(G)の数平均分子量が、ポリスチレン換算で、5,000〜25,000である請求項3または4記載の帯電防止性熱可塑性樹脂組成物。
- 前記ポリエステル(E)が、両末端にカルボキシル基を有する構造である請求項3〜5のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- 前記化合物(D)が、2個以上のエポキシ基を有する多価エポキシ化合物(D)−1、3個以上の水酸基を有する多価アルコール化合物(D)−2、および2個以上のアミノ基を有する多価アミン化合物(D)−3からなる群から選ばれる少なくとも一種である請求項1〜6のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- 前記化合物(C)が、ポリエチレングリコールである請求項1〜7のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- さらに、1種以上のアルカリ金属塩(F)0.01〜5質量部を含有する請求項1〜8のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- 前記熱可塑性樹脂が、ポリオレフィン系樹脂、スチレン系樹脂、ポリエステル系樹脂、ポリエーテル系樹脂、ポリカーボネート系樹脂、ポリアミド系樹脂、および含ハロゲン樹脂からなる群から選ばれる少なくとも一種である請求項1〜9のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物。
- 請求項1〜10のうちいずれか一項記載の帯電防止性熱可塑性樹脂組成物が成形されてなることを特徴とする成形体。
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CN113631622A (zh) * | 2019-03-29 | 2021-11-09 | 株式会社Adeka | 抗静电剂、包含其的抗静电剂组合物、包含这些的抗静电性树脂组合物及其成型体 |
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CN113563561A (zh) * | 2021-08-10 | 2021-10-29 | 广东科力德新材料有限公司 | 用于阴极电泳涂料色浆的树脂及其制备方法、涂料色浆 |
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