JP6649363B2 - 樹脂添加剤組成物および帯電防止性熱可塑性樹脂組成物 - Google Patents
樹脂添加剤組成物および帯電防止性熱可塑性樹脂組成物 Download PDFInfo
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- JP6649363B2 JP6649363B2 JP2017509472A JP2017509472A JP6649363B2 JP 6649363 B2 JP6649363 B2 JP 6649363B2 JP 2017509472 A JP2017509472 A JP 2017509472A JP 2017509472 A JP2017509472 A JP 2017509472A JP 6649363 B2 JP6649363 B2 JP 6649363B2
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- 235000011152 sodium sulphate Nutrition 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
- NTVDGBKMGBRCKB-UHFFFAOYSA-M sodium;12-hydroxyoctadecanoate Chemical compound [Na+].CCCCCCC(O)CCCCCCCCCCC([O-])=O NTVDGBKMGBRCKB-UHFFFAOYSA-M 0.000 description 1
- KVCGISUBCHHTDD-UHFFFAOYSA-M sodium;4-methylbenzenesulfonate Chemical compound [Na+].CC1=CC=C(S([O-])(=O)=O)C=C1 KVCGISUBCHHTDD-UHFFFAOYSA-M 0.000 description 1
- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 229940037312 stearamide Drugs 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- YRGLXIVYESZPLQ-UHFFFAOYSA-I tantalum pentafluoride Chemical compound F[Ta](F)(F)(F)F YRGLXIVYESZPLQ-UHFFFAOYSA-I 0.000 description 1
- IJLNEPWMNHUZEE-UHFFFAOYSA-I tantalum(5+);pentafluoride;hydrofluoride Chemical compound F.[F-].[F-].[F-].[F-].[F-].[Ta+5] IJLNEPWMNHUZEE-UHFFFAOYSA-I 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 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
- HQHCYKULIHKCEB-UHFFFAOYSA-N tetradecanedioic acid Natural products OC(=O)CCCCCCCCCCCCC(O)=O HQHCYKULIHKCEB-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-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
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 239000001017 thiazole dye Substances 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- 239000001003 triarylmethane dye Substances 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- MZHULIWXRDLGRR-UHFFFAOYSA-N tridecyl 3-(3-oxo-3-tridecoxypropyl)sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCC MZHULIWXRDLGRR-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- CENHPXAQKISCGD-UHFFFAOYSA-N trioxathietane 4,4-dioxide Chemical compound O=S1(=O)OOO1 CENHPXAQKISCGD-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
- WTLBZVNBAKMVDP-UHFFFAOYSA-N tris(2-butoxyethyl) phosphate Chemical compound CCCCOCCOP(=O)(OCCOCCCC)OCCOCCCC WTLBZVNBAKMVDP-UHFFFAOYSA-N 0.000 description 1
- LIPMRGQQBZJCTM-UHFFFAOYSA-N tris(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1C(C)C LIPMRGQQBZJCTM-UHFFFAOYSA-N 0.000 description 1
- SPUXJWDKFVXXBI-UHFFFAOYSA-N tris(2-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)(C)C)OC1=CC=CC=C1C(C)(C)C SPUXJWDKFVXXBI-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
- PEXOFOFLXOCMDX-UHFFFAOYSA-N tritridecyl phosphite Chemical compound CCCCCCCCCCCCCOP(OCCCCCCCCCCCCC)OCCCCCCCCCCCCC PEXOFOFLXOCMDX-UHFFFAOYSA-N 0.000 description 1
- KPGXUAIFQMJJFB-UHFFFAOYSA-H tungsten hexachloride Chemical compound Cl[W](Cl)(Cl)(Cl)(Cl)Cl KPGXUAIFQMJJFB-UHFFFAOYSA-H 0.000 description 1
- 239000004762 twaron Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000001018 xanthene dye Substances 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/16—Anti-static materials
-
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
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- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
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- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
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- 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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
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- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
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- 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
- C08K5/56—Organo-metallic compounds, i.e. organic compounds containing a metal-to-carbon bond
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- 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
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
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- Compositions Of Macromolecular Compounds (AREA)
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Description
前記高分子化合物(E)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(B)、および、エポキシ基を2個以上有するエポキシ化合物(D)が、エステル結合を介して結合してなる構造を有し、
前記芳香族リン酸エステル金属塩(H)が、前記一般式(3)中のM2がナトリウムであるナトリウム塩化合物とリチウムであるリチウム塩化合物との混合物であって、ナトリウム塩化合物/リチウム塩化合物=1/4〜4/1の質量比の範囲内であることを特徴とするものである。
(式(3)中、R1〜R4は各々独立に、水素原子または炭素原子数1〜9の直鎖若しくは分岐を有するアルキル基を表し、R5は炭素原子数1〜4のアルキリデン基を表し、M2はアルカリ金属を表す)
(式(5)中、R6は無置換またはヒドロキシ基で置換された炭素原子数1〜40の脂肪族基を表し、M3は、金属原子を表し、nは1〜4の整数であって、M3の金属原子の価数を表す)
前記高分子化合物(E)が、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)で示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(B)と、エポキシ基を2個以上有するエポキシ化合物(D)とが、エステル結合を介して結合してなる構造を有し、
前記化合物(F)が、下記一般式(3)で表される芳香族リン酸エステル金属塩(H)であり、前記高分子化合物(E)100質量部に対し、該芳香族リン酸エステル金属塩(H)から選択される2種以上を、0.001〜50質量部含有し、
前記芳香族リン酸エステル金属塩(H)が、前記一般式(3)中のM2がナトリウムであるナトリウム塩化合物とリチウムであるリチウム塩化合物との混合物であって、ナトリウム塩化合物/リチウム塩化合物=1/4〜4/1の質量比の範囲内であることを特徴とするものである。
(式(2)中、R1〜R4は各々独立に、水素原子または炭素原子数1〜9のアルキル基を表し、R5は炭素原子数1〜4のアルキリデン基を表し、M1はアルカリ金属原子、アルカリ土類金属原子、ベリリウム原子、マグネシウム原子またはアルミニウム原子を表し、M1がアルカリ金属原子である場合、sは1であってかつtは0であり、M1がアルカリ土類金属原子、ベリリウム原子またはマグネシウム原子である場合、sは2であってかつtは0であり、M1がアルミニウム原子である場合、sは1または2であってかつtは3−sである)
(式(3)中、R1〜R4は各々独立に、式(2)中と同じものを表し、R5は、式(2)中と同じものを表し、M2はアルカリ金属を表す)
(式(5)中、R6は無置換またはヒドロキシ基で置換された炭素原子数1〜40の脂肪族基を表し、M3は、金属原子を表し、nは1〜4の整数であって、M3の金属原子の価数を表す)
[本発明の第一の態様の樹脂添加剤組成物および帯電防止性熱可塑性樹脂組成物]
まず、本発明で使用される高分子化合物(E)について説明する。高分子化合物(E)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帯電防止剤である。
本発明で用いる高分子化合物(E)は、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(B)、および、エポキシ基を2個以上有するエポキシ化合物(D)とを、エステル化反応させて製造することができる。
脂肪族ジオールとしては、例えば、1,2−エタンジオール(エチレングリコール)、1,2−プロパンジオール(プロピレングリコール)、1,3−プロパンジオール、1,2−ブタンジオール、1,3−ブタンジオール、2−メチル−1,3−プロパンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、2,2−ジメチル−1,3−プロパンジオール(ネオペンチルグリコール)、2,2−ジエチル−1,3−プロパンジオール(3,3−ジメチロールペンタン)、2−n−ブチル−2−エチル−1,3プロパンジオール(3,3−ジメチロールヘプタン)、3−メチル−1,5−ペンタンジオール、1,6−ヘキサンジオール、2,2,4−トリメチル−1,3−ペンタンジオール、2−エチル−1,3−ヘキサンジオール、2−メチル−1,8−オクタンジオール、1,9−ノナンジオール、1,10−デカンジオール、1,12−オクタデカンジオール、1,4−シクロヘキサンジメタノール、水添ビスフェノールA、1,2−、1,3−または1,4−シクロヘキサンジオール、シクロドデカンジオール、ダイマージオール、水添ダイマージオール、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、ポリエチレングリコール等が挙げられる。
これら脂肪族ジオールの中でも、1,4−シクロヘキサンジメタノール、水添ビスフェノールAが、帯電防止性能の持続性の点から好ましく、1,4−シクロヘキサンジメタノールがより好ましい。
脂肪族ジカルボン酸は、脂肪族ジカルボン酸の誘導体(例えば、酸無水物、アルキルエステル、アルカリ金属塩、酸ハライド等)であってもよく、誘導体を使用してポリエステル(A)を製造した場合は、最終的に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(C)を得るための反応に進んでもよい。また、脂肪族ジカルボン酸およびその誘導体は、2種以上の混合物であってもよい。
芳香族ジカルボン酸は、芳香族ジカルボン酸の誘導体(例えば、酸無水物、アルキルエステル、アルカリ金属塩、酸ハライド等)であってもよく、誘導体を使用してポリエステル(A)を製造した場合は、最終的に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(C)を得るための反応に進んでもよい。また、芳香族ジカルボン酸およびその誘導体は、2種以上の混合物であってもよい。
上記化合物(B)は、親水性を有する化合物が好ましく、下記一般式(6)で表されるポリエチレングリコールが特に好ましい。
上記一般式(6)中、mは5〜250の整数を表す。mは、耐熱性や相溶性の点から、好ましくは20〜150である。
本発明に用いられるエポキシ化合物は、エポキシ基を2個以上有する化合物であれば特に制限されず、例えば、ハイドロキノン、レゾルシン、ピロカテコール、フロログルクシノール等の単核多価フェノール化合物のポリグリシジルエーテル化合物;ジヒドロキシナフタレン、ビフェノール、メチレンビスフェノール(ビスフェノールF)、メチレンビス(オルトクレゾール)、エチリデンビスフェノール、イソプロピリデンビスフェノール(ビスフェノールA)、イソプロピリデンビス(オルトクレゾール)、テトラブロモビスフェノールA、1,3−ビス(4−ヒドロキシクミルベンゼン)、1,4−ビス(4−ヒドロキシクミルベンゼン)、1,1,3−トリス(4−ヒドロキシフェニル)ブタン、1,1,2,2−テトラ(4−ヒドロキシフェニル)エタン、チオビスフェノール、スルホビスフェノール、オキシビスフェノール、フェノールノボラック、オルソクレゾールノボラック、エチルフェノールノボラック、ブチルフェノールノボラック、オクチルフェノールノボラック、レゾルシンノボラック、テルペンフェノール等の多核多価フェノール化合物のポリグリシジルエーテル化合物;エチレングリコール、プロピレングリコール、ブチレングリコール、ヘキサンジオール、ポリエチレングリコール、ポリグリコール、チオジグリコール、グリセリン、トリメチロールプロパン、ペンタエリスリトール、ソルビトール、ビスフェノールA−エチレンオキシド付加物等の多価アルコール類のポリグリシジルエーテル;マレイン酸、フマル酸、イタコン酸、コハク酸、グルタル酸、スベリン酸、アジピン酸、アゼライン酸、セバシン酸、ダイマー酸、トリマー酸、フタル酸、イソフタル酸、テレフタル酸、トリメリット酸、トリメシン酸、ピロメリット酸、テトラヒドロフタル酸、ヘキサヒドロフタル酸、エンドメチレンテトラヒドロフタル酸等の脂肪族、芳香族または脂環族多塩基酸のグリシジルエステル類およびグリシジルメタクリレートの単独重合体または共重合体;N,N−ジグリシジルアニリン、ビス(4−(N−メチル−N−グリシジルアミノ)フェニル)メタン、ジグリシジルオルトトルイジン等のグリシジルアミノ基を有するエポキシ化合物;ビニルシクロヘキセンジエポキシド、ジシクロペンタジエンジエポキサイド、3,4−エポキシシクロヘキシルメチル−3,4−エポキシシクロヘキサンカルボキシレート、3,4−エポキシ−6−メチルシクロヘキシルメチル−6−メチルシクロヘキサンカルボキシレート、ビス(3,4−エポキシ−6−メチルシクロヘキシルメチル)アジペート等の環状オレフィン化合物のエポキシ化物;エポキシ化ポリブタジエン、エポキシ化スチレン−ブタジエン共重合物等のエポキシ化共役ジエン重合体、トリグリシジルイソシアヌレート等の複素環化合物、エポキシ化大豆油等が挙げられる。
また、これらのエポキシ化合物は、末端イソシアネートのプレポリマーによって内部架橋されたもの、あるいは多価の活性水素化合物(多価フェノール、ポリアミン、カルボニル基含有化合物、ポリリン酸エステル等)を用いて高分子量化したものであってもよい。かかるエポキシ化合物は、2種以上を使用してもよい。
上記一般式(7)中、(A)は、上記両末端にカルボキシル基を有するポリエステル(A)から構成されたブロックを表し、(B)は、上記エチレンオキサイド基を一つ以上有し両末端に水酸基を有する化合物(B)から構成されたブロックを表し、uは繰り返し単位の繰り返しの数であり、好ましくは1〜10の数を表す。uは、より好ましくは1〜7の数であり、最も好ましくは1〜5の数である。
高分子化合物(E)を得るためには、上記ブロックポリマー(C)のカルボキシル基と、上記エポキシ化合物のエポキシ基とを反応させればよい。
芳香族リン酸エステル金属塩(H)は、下記一般式(3)または(4)で表される化合物の群から選択される2種以上を用いる。
(式(3)中、R1〜R4は各々独立に、水素原子または炭素原子数1〜9の直鎖若しくは分岐を有するアルキル基を表し、R5は炭素原子数1〜4のアルキリデン基を表し、M2はアルカリ金属を表す)
(式(4)中、R1〜R4は各々独立に、水素原子または炭素原子数1〜9の直鎖若しくは分岐を有するアルキル基を表し、R5は炭素原子数1〜4のアルキリデン基を表す)
上記範囲から外れた場合、本発明の効果が得られなくなるおそれがある。
(式(5)中、R6は無置換またはヒドロキシ基で置換された炭素原子数1〜40の脂肪族基を表し、M3は、金属原子を表し、nは1〜4の整数であって、M3の金属原子の価数を表す)
具体的には、酢酸、プロピオン酸、酪酸、吉草酸、イソ吉草酸、カプロン酸、エナント酸、カプリル酸、ペラルゴン酸、カプリン酸、2−エチルヘキサン酸、ウンデシル酸、ラウリン酸、トリデシル酸、ミリスチン酸、ペンタデシル酸、パルチミン酸、マルガリン酸、ステアリン酸、ノナデシル酸、アラキジン酸、ヘイコシル酸、ベヘン酸、トリコシル酸、リグノセリン酸、セロチン酸、モンタン酸、メリシン酸等の飽和脂肪酸、4−デセン酸、4−ドデセン酸、パルミトレイン酸、α−リノレン酸、リノール酸、γ−リノレン酸、ステアリドン酸、ペトロセリン酸、オレイン酸、エライジン酸、バクセン酸、エイコサペンタエン酸、ドコサペンタエン酸、ドコサヘキサエン酸等の直鎖不飽和脂肪酸、トリメシン酸等の芳香族脂肪酸が挙げられる。
本発明においては、炭素原子数7〜21である脂肪族基が好ましく、特に、ミリスチン酸、ステアリン酸、12−ヒドロキシステアリン酸等の飽和脂肪酸が好ましい。
本発明の熱可塑性樹脂組成物において使用する熱可塑性樹脂としては、いかなるものを用いてもよく、例えば、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、含ハロゲン樹脂が挙げられ、中でも、ポリオレフィン系樹脂が好ましい。かかるポリオレフィン系樹脂としては、例えば、ポリエチレン、低密度ポリエチレン、直鎖状低密度ポリエチレン、高密度ポリエチレン、ポリプロピレン、ホモポリプロピレン、ランダムコポリマーポリプロピレン、ブロックコポリマーポリプロピレン、アイソタクチックポリプロピレン、シンジオタクチックポリプロピレン、ヘミアイソタクチックポリプロピレン、ポリブテン、シクロオレフィンポリマー、ステレオブロックポリプロピレン、ポリ−3−メチル−1−ブテン、ポリ−3−メチル−1−ペンテン、ポリ−4−メチル−1−ペンテン等のα−オレフィン重合体、エチレン−プロピレンのブロックまたはランダム共重合体、インパクトコポリマーポリプロピレン、エチレン−メチルメタクリレート共重合体、エチレン−メチルアクリレート共重合体、エチレン−エチルアクリレート共重合体、エチレン−ブチルアクリレート共重合体、エチレン−酢酸ビニル共重合体等のα−オレフィン共重合体、さらにポリオレフィン系熱可塑性エラストマーが挙げられ、これらの2種以上の共重合体でもよい。
アルカリ金属の例としては、リチウム、ナトリウム、カリウム、セシウム、ルビジウム等が挙げられる。有機酸の例としては、ギ酸、酢酸、プロピオン酸、酪酸、乳酸、ペンタン酸、カプロン酸、ヘプタン酸、カプリル酸、ペラルゴン酸、カプリン酸、ラウリン酸、ミリスチン酸、ペンタデシル酸、パルミチン酸、マルガリン酸、ステアリン酸、12−ヒドロキシステアリン酸等の炭素原子数1〜18の脂肪族モノカルボン酸;シュウ酸、マロン酸、コハク酸、フマル酸、マレイン酸、アジピン酸等の炭素原子数1〜12の脂肪族ジカルボン酸;安息香酸、フタル酸、イソフタル酸、テレフタル酸、サリチル酸等の芳香族カルボン酸;メタンスルホン酸、p−トルエンスルホン酸、ドデシルベンゼンスルホン酸、トリフルオロメタンスルホン酸等の炭素原子数1〜20のスルホン酸等が挙げられる。無機酸の例としては、塩酸、臭化水素酸、硫酸、亜硫酸、リン酸、亜リン酸、ポリリン酸、硝酸、過塩素酸等が挙げられる。中でも、帯電防止性の点から、リチウム、ナトリウム、カリウムがより好ましく、リチウム、ナトリウムが最も好ましい。また、帯電防止性の点から、酢酸の塩、過塩素酸の塩、p−トルエンスルホン酸の塩、ドデシルベンゼンスルホン酸の塩が好ましい。
有機酸の例としては、ギ酸、酢酸、プロピオン酸、酪酸、乳酸等の炭素原子数1〜18の脂肪族モノカルボン酸;シュウ酸、マロン酸、コハク酸、フマル酸、マレイン酸、アジピン酸等の炭素原子数1〜12の脂肪族ジカルボン酸;安息香酸、フタル酸、イソフタル酸、テレフタル酸、サリチル酸等の芳香族カルボン酸;メタンスルホン酸、p−トルエンスルホン酸、ドデシルベンゼンスルホン酸、トリフルオロメタンスルホン酸等の炭素原子数1〜20のスルホン酸等が挙げられる。
無機酸の例としては、塩酸、臭化水素酸、硫酸、亜硫酸、リン酸、亜リン酸、ポリリン酸、硝酸、過塩素酸等が挙げられる。
(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。
フェノール系酸化防止剤を配合する場合の配合量は、熱可塑性樹脂100質量部に対して、0.001〜5質量部が好ましく、0.03〜3質量部がより好ましい。
リン系酸化防止剤を配合する場合の配合量は、熱可塑性樹脂100質量部に対して、0.001〜10質量部が好ましく、0.01〜0.5質量部がより好ましい。
チオエーテル系酸化防止剤を配合する場合の配合量は、熱可塑性樹脂100質量部に対して、0.001〜10質量部が好ましく、0.01〜0.5質量部がより好ましい。
前記紫外線吸収剤を配合する場合の配合量は、熱可塑性樹脂100質量部に対して、0.001〜10質量部が好ましく、0.005〜0.5質量部がより好ましい。
前記ヒンダードアミン化合物を配合する場合の配合量は、熱可塑性樹脂100質量部に対して、0.001〜5質量部が好ましく、0.005〜0.5質量部がより好ましい。
前記造核剤を配合する場合の配合量は、熱可塑性樹脂100質量部に対して、芳香族リン酸エステル金属塩(B)と含めた合計量が0.001〜5質量部が好ましく、0.005〜0.5質量部がより好ましい。
前記難燃剤を配合する場合の配合量は、熱可塑性樹脂100質量部に対して、1〜50質量部が好ましく、10〜30質量部がより好ましい。
前記滑剤を配合する場合の配合量は、熱可塑性樹脂100質量部に対して、0.01〜2質量部が好ましく、0.03〜0.5質量部がより好ましい。
前記充填剤を配合する場合の配合量は、熱可塑性樹脂100質量部に対して、0.01〜80質量部が好ましく、1〜50質量部がより好ましい。
前記金属石鹸を配合する場合の配合量は、熱可塑性樹脂100質量部に対し、金属石鹸0.001〜10質量部が好ましく、0.01〜5質量部がより好ましい。
ここで、一般式(8)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(9)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、前記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。
前記ハイドロタルサイト類を配合する場合の配合量は、熱可塑性樹脂100質量部に対し、0.001〜5質量部が好ましく、0.05〜3質量部がより好ましい。
こうした担体としては、熱可塑性樹脂のフィラーや充填剤として知られているもの、または、常温で固体の難燃剤や光安定剤が使用でき、例えば、ケイ酸カルシウム粉末、シリカ粉末、タルク粉末、アルミナ粉末、酸化チタン粉末、または、これら担体の表面を化学修飾したもの、下記に挙げる難燃剤や酸化防止剤の中で固体のもの等が挙げられる。これらの担体の中でも担体の表面を化学修飾したものが好ましく、シリカ粉末の表面を化学修飾したものがより好ましい。これらの担体は、平均粒径が0.1〜100μmのものが好ましく、0.5〜50μmのものがより好ましい。
また、前記高分子化合物(E)は、ブロックポリマー(C)と、上記エポキシ化合物(D)のエポキシ基とを樹脂成分に練り込みながら前記高分子化合物(E)を合成して配合してもよく、そのときにアルカリ金属塩(G)を同時に練り込んでもよく、また、射出成形等の成形時に高分子化合物(E)とアルカリ金属塩(G)と樹脂成分とを混合して成型品を得る方法で配合してもよく、さらに、あらかじめ一般式(3)または(4)で表される芳香族リン酸エステル金属塩(H)、および/または、アルカリ金属塩(G)と熱可塑性樹脂とのマスターバッチを製造しておき、このマスターバッチを配合してもよい。
本発明の成形体は、本発明の熱可塑性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、帯電防止性を有する樹脂成形体を得ることができる。成形方法としては、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。
以下、本発明について、詳細に説明する。
まず、本発明の帯電防止性熱可塑性樹脂組成物について説明する。本発明の樹脂組成物は、熱可塑性樹脂100質量部に対して、1種以上の高分子化合物(E)3〜60質量部と、下記一般式(2)で表される1種以上の化合物(F)0.001〜10質量部とを含有するものである。本発明の樹脂組成物においては、高分子化合物(E)が、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)で示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(B)と、エポキシ基を2個以上有するエポキシ化合物(D)とが、エステル結合を介して結合してなる構造を有する。
(式(2)中、R1〜R4は各々独立に、水素原子または炭素原子数1〜9のアルキル基を表し、R5は炭素原子数1〜4のアルキリデン基を表し、M1はアルカリ金属原子、アルカリ土類金属原子、ベリリウム原子、マグネシウム原子またはアルミニウム原子を表し、M1がアルカリ金属原子である場合、sは1であってかつtは0であり、M1がアルカリ土類金属原子、ベリリウム原子またはマグネシウム原子である場合、sは2であってかつtは0であり、M1がアルミニウム原子である場合、sは1または2であってかつtは3−sである)
本発明の樹脂組成物において使用する熱可塑性樹脂としては、第一の態様において挙げたのと同様のものを用いることができる。
本発明で用いられるジオールとしては、脂肪族ジオール、芳香族基含有ジオールが挙げられる。また、ジオールは、2種以上の混合物でもよい。脂肪族ジオールとしては、第一の態様において挙げたのと同様のものを用いることができる。
本発明で用いられる脂肪族ジカルボン酸は、脂肪族ジカルボン酸の誘導体(例えば、酸無水物、アルキルエステル、アルカリ金属塩、酸ハライド等)であってもよい。脂肪族ジカルボン酸およびその誘導体は、2種以上の混合物でもよい。
本発明で用いられる芳香族ジカルボン酸は、芳香族ジカルボン酸の誘導体(例えば、酸無水物、アルキルエステル、アルカリ金属塩、酸ハライド等)であってもよい。また、芳香族ジカルボン酸およびその誘導体は、2種以上の混合物でもよい。
上記一般式(6)中、mは5〜250の数を表す。mは、耐熱性や相溶性の点から、好ましくは20〜150である。
上記一般式(7)中、(A)は、上記両末端にカルボキシル基を有するポリエステル(A)から構成されたブロックを表し、(B)は、上記両末端に水酸基を有する化合物(B)から構成されたブロックを表し、uは繰り返し単位の繰り返しの数であり、好ましくは1〜10の数を表す。uは、より好ましくは1〜7の数であり、最も好ましくは1〜5の数である。
(式(3)中、R1〜R4は各々独立に、式(2)中と同じものを表し、R5は、式(2)中と同じものを表し、M2はアルカリ金属を表す)
(式(4)中、R1〜R5は、式(3)と同じものを表す)
上記範囲から外れた場合、本発明の効果が十分に得られなくなるおそれがある。
(式(5)中、R6は無置換またはヒドロキシ基で置換された炭素原子数1〜40の脂肪族基を表し、M3は、金属原子を表し、nは1〜4の整数であって、M3の金属原子の価数を表す)
具体的には、酢酸、プロピオン酸、酪酸、吉草酸、イソ吉草酸、カプロン酸、エナント酸、カプリル酸、ペラルゴン酸、カプリン酸、2−エチルヘキサン酸、ウンデシル酸、ラウリン酸、トリデシル酸、ミリスチン酸、ペンタデシル酸、パルチミン酸、マルガリン酸、ステアリン酸、ノナデシル酸、アラキジン酸、ヘイコシル酸、ベヘン酸、トリコシル酸、リグノセリン酸、セロチン酸、モンタン酸、メリシン酸等の飽和脂肪酸、4−デセン酸、4−ドデセン酸、パルミトレイン酸、α−リノレン酸、リノール酸、γ−リノレン酸、ステアリドン酸、ペトロセリン酸、オレイン酸、エライジン酸、バクセン酸、エイコサペンタエン酸、ドコサペンタエン酸、ドコサヘキサエン酸等の直鎖不飽和脂肪酸、トリメシン酸等の芳香族脂肪酸が挙げられる。
本発明においては、炭素原子数7〜21である脂肪族基が好ましく、特に、ミリスチン酸、ステアリン酸、12−ヒドロキシステアリン酸等の飽和脂肪酸が好ましい。
アルカリ金属およびアルカリ金属の塩の具体例としては、第一の態様において挙げたのと同様のものを用いることができる。
以下、本発明を実施例により、具体的に説明する。
〔製造例1−1〕
(高分子化合物(E)−1−1の製造)
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420g、脂肪族ジカルボン酸として、アジピン酸を485g、芳香族ジカルボン酸として、イソフタル酸を0.5g、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0.5g、酢酸ジルコニウムを0.5g仕込み、160℃から200℃まで徐々に昇温しながら常圧で4時間、その後200℃、減圧下で3時間重合して、ポリエステル(A)−1−1を得た。ポリエステル(A)−1−1の酸価は56、数平均分子量Mnはポリスチレン換算で3,200であった。
(高分子化合物(E)−1−2の製造)
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490g、脂肪族ジカルボン酸として、アジピン酸を524g、芳香族ジカルボン酸として、無水フタル酸を0.5g、酸化防止剤(アデカスタブAO−60)を0.5g仕込み、160℃〜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(A)−1−2を得た。ポリエステル(A)−1−2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。
(高分子化合物(E)−1−3の製造)
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)、エチレンオキサイド基を一つ以上有し両末端に水酸基を有する化合物(B)として、数平均分子量2,000のポリエチレングリコール((B)−1−1)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、ブロックポリマー(C)−1−3を得た。このブロックポリマー(C)−1−3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。
230℃におけるMFR=8g/10minのホモポリプロピレンに対し、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」)0.05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」)0.05質量部、ステアリン酸カルシウム0.05質量部、および、下記の表1〜2中に示す配合量に基づいて各成分を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40℃の加工条件で成形し、表面固有抵抗値測定用試験片(100mm×100mm×3mm)を作製した。
得られた表面固有抵抗値測定用試験片(100mm×100mm×3mm)を、成形加工後直ちに、温度25℃、湿度60%RHの条件下にて1日保存し、保存後、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各々表1および表2に示す。
(H)−1−2:リチウム−2,2’−メチレンビス(4,6−ジ−tert−ブチルフェニル)ホスフェート
(H)−1−3:アルミニウムヒドロキシビス[2,2’−メチレンビス(4,6−ジ−tert−ブチルフェニル)ホスフェート]
(I)−1−1:ミリスチン酸リチウム
(I)−1−2:ステアリン酸リチウム
(G)−1−1:ドデシルベンゼンスルホン酸ナトリウム
(G)−1−2:p−トルエンスルホン酸リチウム
以下、本発明を実施例により、具体的に説明する。なお、以下の実施例等において、「%」および「ppm」は、特に記載がない限り、質量基準である。
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)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)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、1,4−シクロヘキサンジメタノールを656g、アジピン酸を708g(4.85モル)、無水フタル酸を0.7g(0.01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、アデカスタブAO−60(株)、ADEKA製)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(A)−2−1を得た。ポリエステル(A)−2−1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、1,4−ビス(β−ヒドロキシエトキシ)ベンゼンを370g、アジピン酸を289g(1.98モル)、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(A)−2−2を得た。ポリエステル(A)−2−2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、ビスフェノールAのエチレンオキサイド付加物を591g、セバシン酸を235g(1.16モル)、イソフタル酸を8g(0.05モル)、両末端に水酸基を有する化合物(B)−2−2として数平均分子量2,000のポリエチレングリコールを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基を有する構造を有するブロックポリマー(C)−2−3を得た。この両末端にカルボキシル基を有する構造を有するブロックポリマー(C)−2−3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。
下記の表3〜6に記載した配合量(質量部)に基づいてブレンドした樹脂組成物を用いて、下記に示す試験片作製条件に従い、試験片を得た。得られた試験片を用いて、下記に従い、表面固有抵抗値(SR値)の測定と、耐水拭き性試験を行った。
また、試験片作製時に得られたペレットを用いて、下記に従い、結晶化温度を測定した。
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」0.05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」0.05質量部、ステアリン酸カルシウム0.05質量部、および、下記の表3〜6中に示す配合量に基づいてブレンドした樹脂組成物を、(株)池貝製の2軸押出機(PCM30,60mesh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、横型射出成形機(NEX80:日精樹脂工業(株)製)を用い、樹脂温度230℃、金型温度40℃の加工条件で成形し、表面固有抵抗値測定用試験片(100mm×100mm×3mm)と、曲げ弾性率、シャルピー衝撃強度および熱変形温度の測定用試験片(80mm×10mm×4mm)とを得た。
得られた表面固有抵抗値測定用試験片(100mm×100mm×3mm)を、成形加工後直ちに、温度25℃、湿度60%RHの条件下に保存し、成形加工の1日および30日保存後に、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。
得られた試験片の表面を流水中ウエスで50回拭いた後、25℃、湿度60%に調整された恒温恒湿槽内に24時間静置し、その後、アドバンテスト社製、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点で行い、その平均値を求めた。
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、10℃/分の速度で230℃まで昇温し、5分間保持後、−10℃/分の速度で50℃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。
ISO178に準拠して測定した。
ISO179−1(ノッチ付)に準拠して測定した。
ISO75−2に準拠して測定した。
*2:ドデシルベンゼンスルホン酸ナトリウム
*3:p−トルエンスルホン酸リチウム
*4:ステアリン酸リチウム
Claims (20)
- 高分子化合物(E)100質量部に対し、下記一般式(3)で表される芳香族リン酸エステル金属塩(H)から選択される2種以上を、0.001〜50質量部含有する樹脂添加剤組成物であって、
前記高分子化合物(E)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(B)、および、エポキシ基を2個以上有するエポキシ化合物(D)が、エステル結合を介して結合してなる構造を有し、
前記芳香族リン酸エステル金属塩(H)が、前記一般式(3)中のM 2 がナトリウムであるナトリウム塩化合物とリチウムであるリチウム塩化合物との混合物であって、ナトリウム塩化合物/リチウム塩化合物=1/4〜4/1の質量比の範囲内であることを特徴とする樹脂添加剤組成物。
(式(3)中、R1〜R4は各々独立に、水素原子または炭素原子数1〜9の直鎖若しくは分岐を有するアルキル基を表し、R5は炭素原子数1〜4のアルキリデン基を表し、M2はアルカリ金属を表す) - 前記高分子化合物(E)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(A)と、前記化合物(B)と、前記エポキシ化合物(D)とが、エステル結合を介して結合してなる構造を有する請求項1または2記載の樹脂添加剤組成物。
- 前記高分子化合物(E)が、前記ポリエステル(A)から構成されたブロックおよび前記化合物(B)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(C)と、前記エポキシ化合物(D)とがエステル結合を介して結合してなる構造を有する請求項3記載の樹脂添加剤組成物。
- 前記ポリエステル(A)が、両末端にカルボキシル基を有する構造を有する請求項3記載の樹脂添加剤組成物。
- 前記ポリエステル(A)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(B)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(C)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4記載の樹脂添加剤組成物。
- 前記化合物(B)が、ポリエチレングリコールである請求項1記載の樹脂添加剤組成物。
- 熱可塑性樹脂100質量部に対して、1種以上の高分子化合物(E)3〜60質量部と、下記一般式(2)で表される1種以上の化合物(F)0.001〜10質量部とを含有する帯電防止性熱可塑性樹脂組成物であって、
前記高分子化合物(E)が、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)で示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(B)と、エポキシ基を2個以上有するエポキシ化合物(D)とが、エステル結合を介して結合してなる構造を有し、
前記化合物(F)が、下記一般式(3)で表される芳香族リン酸エステル金属塩(H)であり、前記高分子化合物(E)100質量部に対し、該芳香族リン酸エステル金属塩(H)から選択される2種以上を、0.001〜50質量部含有し、
前記芳香族リン酸エステル金属塩(H)が、前記一般式(3)中のM 2 がナトリウムであるナトリウム塩化合物とリチウムであるリチウム塩化合物との混合物であって、ナトリウム塩化合物/リチウム塩化合物=1/4〜4/1の質量比の範囲内であることを特徴とする帯電防止性熱可塑性樹脂組成物。
(式(2)中、R1〜R4は各々独立に、水素原子または炭素原子数1〜9のアルキル基を表し、R5は炭素原子数1〜4のアルキリデン基を表し、M1はアルカリ金属原子、アルカリ土類金属原子、ベリリウム原子、マグネシウム原子またはアルミニウム原子を表し、M1がアルカリ金属原子である場合、sは1であってかつtは0であり、M1がアルカリ土類金属原子、ベリリウム原子またはマグネシウム原子である場合、sは2であってかつtは0であり、M1がアルミニウム原子である場合、sは1または2であってかつtは3−sである)
(式(3)中、R 1 〜R 4 は各々独立に、式(2)中と同じものを表し、R 5 は、式(2)中と同じものを表し、M 2 はアルカリ金属を表す) - 前記高分子化合物(E)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(A)と、前記化合物(B)と、前記エポキシ化合物(D)とが、エステル結合を介して結合してなる構造を有する請求項8または9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(E)が、前記ポリエステル(A)から構成されたブロックおよび前記化合物(B)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(C)と、前記エポキシ化合物(D)とが、エステル結合を介して結合してなる構造を有する請求項10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(E)を構成する前記ポリエステル(A)が、両末端にカルボキシル基を有する構造を有する請求項10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(E)における、前記ポリエステル(A)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(B)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(C)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11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(E)を構成する前記化合物(B)が、ポリエチレングリコールである請求項8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の塩(G)を、前記熱可塑性樹脂100質量部に対し、0.01〜5質量部含有する請求項8または9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の塩(G)を、前記熱可塑性樹脂100質量部に対し、0.01〜5質量部含有する請求項11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である請求項8記載の帯電防止性熱可塑性樹脂組成物。
- 請求項10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。
- 請求項11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。
- 請求項15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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