JP2010150393A - Polylactic acid composition and molded article of the same - Google Patents
Polylactic acid composition and molded article of the same Download PDFInfo
- Publication number
- JP2010150393A JP2010150393A JP2008330122A JP2008330122A JP2010150393A JP 2010150393 A JP2010150393 A JP 2010150393A JP 2008330122 A JP2008330122 A JP 2008330122A JP 2008330122 A JP2008330122 A JP 2008330122A JP 2010150393 A JP2010150393 A JP 2010150393A
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- acid
- resin
- Prior art date
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- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 115
- 229920000747 poly(lactic acid) Polymers 0.000 title claims abstract description 98
- 239000004626 polylactic acid Substances 0.000 title claims abstract description 98
- -1 phosphono fatty acid ester Chemical class 0.000 claims abstract description 212
- 229920005989 resin Polymers 0.000 claims abstract description 88
- 239000011347 resin Substances 0.000 claims abstract description 88
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 70
- 239000000194 fatty acid Substances 0.000 claims abstract description 70
- 229930195729 fatty acid Natural products 0.000 claims abstract description 70
- 238000004519 manufacturing process Methods 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 19
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 18
- 150000002989 phenols Chemical class 0.000 claims abstract description 12
- 150000003568 thioethers Chemical class 0.000 claims abstract description 10
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims abstract description 9
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 62
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 239000003063 flame retardant Substances 0.000 claims description 52
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 47
- 238000002844 melting Methods 0.000 claims description 44
- 230000008018 melting Effects 0.000 claims description 44
- 229910052751 metal Inorganic materials 0.000 claims description 40
- 239000002184 metal Substances 0.000 claims description 40
- JVTAAEKCZFNVCJ-UWTATZPHSA-N D-lactic acid Chemical compound C[C@@H](O)C(O)=O JVTAAEKCZFNVCJ-UWTATZPHSA-N 0.000 claims description 34
- 229920001432 poly(L-lactide) Polymers 0.000 claims description 34
- 239000000113 methacrylic resin Substances 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
- 229940022769 d- lactic acid Drugs 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical group C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 22
- 229910019142 PO4 Inorganic materials 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000010452 phosphate Substances 0.000 claims description 20
- 239000004609 Impact Modifier Substances 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000005259 measurement Methods 0.000 claims description 15
- 229910052725 zinc Inorganic materials 0.000 claims description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims description 13
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
- 150000001342 alkaline earth metals Chemical group 0.000 claims description 12
- 238000001746 injection moulding Methods 0.000 claims description 12
- 238000004898 kneading Methods 0.000 claims description 12
- 230000014759 maintenance of location Effects 0.000 claims description 12
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 12
- 239000004593 Epoxy Substances 0.000 claims description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 11
- 239000011256 inorganic filler Substances 0.000 claims description 11
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 11
- 239000011574 phosphorus Substances 0.000 claims description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical group [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 150000001340 alkali metals Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 8
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 7
- 238000001125 extrusion Methods 0.000 claims description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 claims description 5
- 239000002981 blocking agent Substances 0.000 claims description 5
- 230000000630 rising effect Effects 0.000 claims description 5
- 239000012298 atmosphere Substances 0.000 claims description 4
- 238000000071 blow moulding Methods 0.000 claims description 2
- 238000010097 foam moulding Methods 0.000 claims description 2
- 238000003856 thermoforming Methods 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 229910001463 metal phosphate Inorganic materials 0.000 abstract 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 description 61
- 239000005060 rubber Substances 0.000 description 52
- 229920001577 copolymer Polymers 0.000 description 49
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 44
- 238000000465 moulding Methods 0.000 description 34
- 229920002554 vinyl polymer Polymers 0.000 description 32
- 150000004665 fatty acids Chemical class 0.000 description 28
- 238000006116 polymerization reaction Methods 0.000 description 28
- 238000010438 heat treatment Methods 0.000 description 27
- 229920000642 polymer Polymers 0.000 description 25
- 239000000835 fiber Substances 0.000 description 24
- 239000000178 monomer Substances 0.000 description 24
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 24
- 239000004810 polytetrafluoroethylene Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- 230000009477 glass transition Effects 0.000 description 22
- 239000000843 powder Substances 0.000 description 22
- 239000004014 plasticizer Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 20
- 150000002148 esters Chemical class 0.000 description 20
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 19
- 239000012071 phase Substances 0.000 description 19
- 235000021317 phosphate Nutrition 0.000 description 19
- 239000002245 particle Substances 0.000 description 18
- 229920001955 polyphenylene ether Polymers 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 17
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 16
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 15
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 15
- 239000011734 sodium Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 235000006708 antioxidants Nutrition 0.000 description 14
- 239000013078 crystal Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 238000002425 crystallisation Methods 0.000 description 13
- 230000008025 crystallization Effects 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- 229920000728 polyester Polymers 0.000 description 11
- 230000002829 reductive effect Effects 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 230000000704 physical effect Effects 0.000 description 10
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical group OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- 229930182843 D-Lactic acid Natural products 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 9
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 9
- 229920000800 acrylic rubber Polymers 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
- 230000008859 change Effects 0.000 description 9
- 239000002131 composite material Substances 0.000 description 9
- 239000006185 dispersion Substances 0.000 description 9
- 239000000806 elastomer Substances 0.000 description 9
- 239000008188 pellet Substances 0.000 description 9
- 229920000058 polyacrylate Polymers 0.000 description 9
- 229910052708 sodium Inorganic materials 0.000 description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- 229920000388 Polyphosphate Polymers 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 8
- 229910052791 calcium Inorganic materials 0.000 description 8
- 239000011575 calcium Substances 0.000 description 8
- 229920003244 diene elastomer Polymers 0.000 description 8
- 229910052749 magnesium Inorganic materials 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- 230000036961 partial effect Effects 0.000 description 8
- 239000001205 polyphosphate Substances 0.000 description 8
- 235000011176 polyphosphates Nutrition 0.000 description 8
- 229920001296 polysiloxane Polymers 0.000 description 8
- 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 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 7
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 125000000732 arylene group Chemical group 0.000 description 7
- 229920001400 block copolymer Polymers 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 238000011109 contamination Methods 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 235000011187 glycerol Nutrition 0.000 description 7
- 229920000578 graft copolymer Polymers 0.000 description 7
- 229910052744 lithium Inorganic materials 0.000 description 7
- 239000002667 nucleating agent Substances 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002202 Polyethylene glycol Substances 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 230000006866 deterioration Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 6
- 229920002313 fluoropolymer Polymers 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 6
- UTOPWMOLSKOLTQ-UHFFFAOYSA-N octacosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC(O)=O UTOPWMOLSKOLTQ-UHFFFAOYSA-N 0.000 description 6
- 239000012766 organic filler Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 229920001223 polyethylene glycol Polymers 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000010703 silicon Substances 0.000 description 6
- 229910052710 silicon Inorganic materials 0.000 description 6
- 229920001169 thermoplastic Polymers 0.000 description 6
- 239000004416 thermosoftening plastic Substances 0.000 description 6
- 239000002023 wood Substances 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- JJTUDXZGHPGLLC-IMJSIDKUSA-N 4511-42-6 Chemical compound C[C@@H]1OC(=O)[C@H](C)OC1=O JJTUDXZGHPGLLC-IMJSIDKUSA-N 0.000 description 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 5
- 229920000297 Rayon Polymers 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 239000002216 antistatic agent Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000010903 husk Substances 0.000 description 5
- 239000004310 lactic acid Substances 0.000 description 5
- 235000014655 lactic acid Nutrition 0.000 description 5
- 150000004692 metal hydroxides Chemical class 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 229920000620 organic polymer Polymers 0.000 description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 5
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- 239000002904 solvent Substances 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 4
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- ZSTLPJLUQNQBDQ-UHFFFAOYSA-N azanylidyne(dihydroxy)-$l^{5}-phosphane Chemical compound OP(O)#N ZSTLPJLUQNQBDQ-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 125000002993 cycloalkylene group Chemical group 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- YMMRWISVGIRFGG-UHFFFAOYSA-N ethyl 2-dihexoxyphosphorylacetate Chemical compound CCCCCCOP(=O)(CC(=O)OCC)OCCCCCC YMMRWISVGIRFGG-UHFFFAOYSA-N 0.000 description 4
- 239000004811 fluoropolymer Substances 0.000 description 4
- 239000010439 graphite Substances 0.000 description 4
- 229910002804 graphite Inorganic materials 0.000 description 4
- 229920005669 high impact polystyrene Polymers 0.000 description 4
- 239000004797 high-impact polystyrene Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
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- 239000012535 impurity Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
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- AJHKJOCIGPIJFZ-UHFFFAOYSA-N tris(2,6-ditert-butylphenyl) phosphite Chemical compound CC(C)(C)C1=CC=CC(C(C)(C)C)=C1OP(OC=1C(=CC=CC=1C(C)(C)C)C(C)(C)C)OC1=C(C(C)(C)C)C=CC=C1C(C)(C)C AJHKJOCIGPIJFZ-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
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- QFGXDXGDZKTYFD-UHFFFAOYSA-N tris[2,3-di(propan-2-yl)phenyl] phosphite Chemical compound CC(C)C1=CC=CC(OP(OC=2C(=C(C(C)C)C=CC=2)C(C)C)OC=2C(=C(C(C)C)C=CC=2)C(C)C)=C1C(C)C QFGXDXGDZKTYFD-UHFFFAOYSA-N 0.000 description 1
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- 239000010698 whale oil Substances 0.000 description 1
- 239000002025 wood fiber Substances 0.000 description 1
- 210000002268 wool Anatomy 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
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
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Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Biological Depolymerization Polymers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
Description
本発明は、ポリ乳酸組成物に関する。さらに詳しくは、本発明は、熱安定性、特に湿熱安定性に優れたポリ乳酸組成物およびその成形品に関する。 The present invention relates to a polylactic acid composition. More specifically, the present invention relates to a polylactic acid composition excellent in heat stability, particularly wet heat stability, and a molded product thereof.
近年、地球環境保護の目的から、自然環境下で分解される生分解性ポリマーが注目され、世界中で研究されている。生分解性ポリマーとして、ポリ乳酸、ポリヒドロキシブチレート、ポリカプロラクトンなどの脂肪族ポリエステルが知られている。ポリ乳酸は、生体由来の原料から得られる乳酸あるいはその誘導体を原料とするため生体安全性が高く、環境にやさしい高分子材料である。そのため汎用ポリマーとしての利用が検討され、延伸フィルム、繊維、射出成形品などとしての利用が検討されている。また、利用の幅を広げるため、各種ポリマーアロイの検討も幅広く行われてきた。
しかしながらポリ乳酸は、結晶融解温度が約155℃と低いため耐熱性に限界がある。また、熱安定性、特に湿熱安定性が悪く、湿度により分解されやすいという欠点がある。
In recent years, for the purpose of protecting the global environment, biodegradable polymers that are decomposed in a natural environment have attracted attention and are being studied all over the world. As biodegradable polymers, aliphatic polyesters such as polylactic acid, polyhydroxybutyrate, and polycaprolactone are known. Since polylactic acid uses lactic acid obtained from a raw material derived from a living body or a derivative thereof as a raw material, it is a high-safety and environmentally friendly polymer material. Therefore, the use as a general-purpose polymer is examined, and the use as a stretched film, a fiber, an injection molded product, etc. is examined. In addition, various polymer alloys have been extensively studied in order to expand the range of use.
However, since polylactic acid has a low crystal melting temperature of about 155 ° C., its heat resistance is limited. In addition, the thermal stability, particularly wet heat stability is poor, and there is a drawback that it is easily decomposed by humidity.
一方、L−乳酸単位からなるポリL−乳酸(PLLA)と、D−乳酸単位からなるポリD−乳酸(PDLA)とを溶液あるいは溶融状態で混合することにより、ステレオコンプレックスポリ乳酸が形成されることが知られている(特許文献1および非特許文献1)。このステレオコンプレックスポリ乳酸は、結晶融解温度が200〜230℃とPLLAやPDLAに比べて融点が高く、結晶性も高いことが知られている。 On the other hand, a stereocomplex polylactic acid is formed by mixing poly L-lactic acid (PLLA) composed of L-lactic acid units and poly D-lactic acid (PDLA) composed of D-lactic acid units in a solution or in a molten state. It is known (Patent Literature 1 and Non-Patent Literature 1). It is known that this stereocomplex polylactic acid has a crystal melting temperature of 200 to 230 ° C., a higher melting point than PLLA and PDLA, and high crystallinity.
しかしながらステレオコンプレックスポリ乳酸の形成は容易ではなく、とりわけPLLAやPDLAの重量平均分子量が15万を超えるとその困難さはいっそう顕著となる(特許文献1)。即ち、ステレオコンプレックスポリ乳酸は、通常、単一相を示すことはなく、PLLAおよびPDLA相(ホモ相)と、ポリ乳酸ステレオコンプレックス相(コンプレックス相)の混合相組成物となる。この混合組成物において、コンプレックス相の割合が少ないとステレオコンプレックスポリ乳酸本来の耐熱性を発揮することが困難である。また、ステレオコンプレックスポリ乳酸も、ポリ乳酸ホモポリマーと同様、脂肪族ポリエステルの特徴として、湿度により加水分解を受けやすい欠点を有している。 However, the formation of stereocomplex polylactic acid is not easy, and the difficulty becomes even more remarkable when the weight average molecular weight of PLLA or PDLA exceeds 150,000 (Patent Document 1). That is, the stereocomplex polylactic acid usually does not show a single phase, but becomes a mixed phase composition of PLLA and PDLA phases (homophase) and a polylactic acid stereocomplex phase (complex phase). In this mixed composition, if the ratio of the complex phase is small, it is difficult to exhibit the heat resistance inherent in stereocomplex polylactic acid. Similarly to polylactic acid homopolymer, stereocomplex polylactic acid also has the disadvantage of being easily hydrolyzed by humidity as a feature of aliphatic polyester.
このような現状を打開すべく、ポリ乳酸の熱安定性向上について種々検討がなされてきた。例えば、特許文献2には、分子量が5万以上に達した時点で、ポリ乳酸に触媒失活剤としてリン酸系化合物、或いは亜リン酸系化合物を添加することが提案されている。また特許文献3および4には、触媒失活剤として酸性リン酸エステル類またはキレート剤を添加し、ポリ乳酸の熱安定性を向上することが教示されている。しかしながら、特許文献2の如く低分子量のポリ乳酸に、触媒失活剤を添加することは、その後の重合反応が阻害され、高分子量体が得られないことを意味する。一方、特許文献3および4に記載の酸性リン酸エステルは、その酸性度のために製造設備の腐食、或いは樹脂の湿熱安定性を低下させる原因となる。また例示されているキレート剤は概ね耐熱性に乏しく、金属触媒を捕捉する前に焦成し、重大な着色や悪臭の原因となる。 Various studies have been made on improving the thermal stability of polylactic acid in order to overcome this situation. For example, Patent Document 2 proposes adding a phosphoric acid compound or a phosphorous acid compound as a catalyst deactivator to polylactic acid when the molecular weight reaches 50,000 or more. Patent Documents 3 and 4 teach that an acid phosphate ester or a chelating agent is added as a catalyst deactivator to improve the thermal stability of polylactic acid. However, the addition of a catalyst deactivator to low molecular weight polylactic acid as in Patent Document 2 means that the subsequent polymerization reaction is inhibited and a high molecular weight product cannot be obtained. On the other hand, the acidic phosphoric acid esters described in Patent Documents 3 and 4 cause the corrosion of the production equipment or the wet heat stability of the resin due to its acidity. Further, the exemplified chelating agents are generally poor in heat resistance, and are scorched before capturing the metal catalyst, causing serious coloring and malodor.
特許文献5には、ポリ乳酸にホスホノ脂肪酸エステルを含有させることにより、ポリ乳酸中の残留触媒を効果的に失活でき、ポリ乳酸熱安定性が改善することが提案されている。しかしながら、湿熱安定性に関して検討はされておらず、湿度により加水分解されやすいという脂肪族ポリエステル特有の特徴に対して十分な対策が取られていない。 Patent Document 5 proposes that by containing a phosphono fatty acid ester in polylactic acid, the residual catalyst in the polylactic acid can be effectively deactivated, and the thermal stability of polylactic acid is improved. However, no consideration has been given to wet heat stability, and sufficient measures have not been taken for the characteristic feature of aliphatic polyesters that they are easily hydrolyzed by humidity.
本発明の目的は、熱安定性、特に湿熱安定性に優れたポリ乳酸組成物およびその成形品を提供することにある。また本発明の目的は、熱安定性、特に湿熱安定性に優れたポリ乳酸組成物の製造方法を提供することにある。 An object of the present invention is to provide a polylactic acid composition excellent in heat stability, particularly wet heat stability, and a molded product thereof. Another object of the present invention is to provide a method for producing a polylactic acid composition having excellent heat stability, particularly wet heat stability.
本発明者は、ポリ乳酸の熱安定性、特に湿熱安定性を向上させることについて鋭意検討した。その結果、ポリ乳酸の熱安定性を低下させると考えられる残留触媒の失活剤としてホスホノ脂肪酸エステル(B成分)を用い、さらにリン酸エステル金属塩(C成分)を結晶核剤として用い、特定の酸化防止剤(D成分)を用いると、ホスホノ脂肪酸エステル(B成分)の失活効果が相乗的に高まり、熱安定性、特に湿熱安定性に優れたポリ乳酸組成物が得られることを見出した。更には、作業環境や使用環境の悪化原因となる末端封鎖剤由来の悪臭や悪臭原因物質由来と思われる金型汚染を低減させ、驚くべきことに、一定の湿熱安定性を発揮するために必要な末端封鎖剤(E成分)の添加量が低減できることを見出した。 The present inventor has intensively studied on improving the thermal stability, particularly wet heat stability, of polylactic acid. As a result, phosphono fatty acid ester (component B) is used as a deactivator for residual catalyst, which is considered to reduce the thermal stability of polylactic acid, and phosphoric acid ester metal salt (component C) is used as a crystal nucleating agent. It has been found that the use of an antioxidant (D component) synergistically increases the deactivation effect of the phosphono fatty acid ester (B component), and a polylactic acid composition excellent in thermal stability, particularly wet heat stability, can be obtained. It was. Furthermore, it is necessary to reduce the foul odor derived from the end-capping agent and the mold contamination that seems to be caused by the foul odor-causing substances that cause deterioration of the working environment and use environment, and surprisingly, it is necessary to demonstrate a certain degree of wet heat stability. It has been found that the amount of the end-capping agent (E component) added can be reduced.
また、ポリ乳酸へのホスホノ脂肪酸エステル(B成分)の添加は、ポリ乳酸の重合終了時のみならず、他の添加剤成分と混練してポリ乳酸組成物を調製する際にも行うと、熱に曝されていない新鮮な触媒失活剤を添加することにより、高効率な失活効果が得られ、更に高レベルな熱安定性、特に湿熱安定性に優れたポリ乳酸組成物が得られることを見出し、かつポリ乳酸とメタクリル系樹脂とのポリマーアロイにより湿熱処理後の寸法変化が抑えられ、寸法安定性が高く産業上の有用性が高い成形品を効率よく与えることを見出し、本発明を完成した。 In addition, the addition of phosphono fatty acid ester (component B) to polylactic acid is not only at the end of polymerization of polylactic acid but also when kneaded with other additive components to prepare a polylactic acid composition. By adding a fresh catalyst deactivator that has not been exposed to water, a highly efficient deactivation effect can be obtained, and a polylactic acid composition having a high level of thermal stability, in particular wet heat stability, can be obtained. And found that the polymer alloy of polylactic acid and methacrylic resin suppresses dimensional change after wet heat treatment, and efficiently gives a molded product having high dimensional stability and high industrial usefulness. completed.
即ち本発明は、100重量部のポリ乳酸(A−α成分)5〜95重量%とメタクリル系樹脂(A−β成分)95〜5重量%からなる樹脂成分(A成分)、
0.001〜5重量部のホスホノ脂肪酸エステル(B成分)、
0.01〜5重量部のリン酸エステル金属塩(C成分)、
0.001〜2重量部の、ホスファイト系化合物、ホスホナイト系化合物、ヒンダートフェノール系化合物およびチオエーテル系化合物からなる群より選ばれる少なくとも一種の酸化防止剤(D成分)、並びに
0.001〜10重量部の末端封鎖剤(E成分、)
を含有する組成物である。
That is, the present invention is a resin component (component A) comprising 100 parts by weight of polylactic acid (A-α component) 5 to 95% by weight and methacrylic resin (A-β component) 95 to 5% by weight,
0.001 to 5 parts by weight of a phosphono fatty acid ester (component B),
0.01-5 parts by weight of a phosphate metal salt (component C),
0.001 to 2 parts by weight of at least one antioxidant (D component) selected from the group consisting of phosphite compounds, phosphonite compounds, hindered phenol compounds and thioether compounds, and 0.001 to 10 Part by weight of end-capping agent (E component)
It is a composition containing this.
また本発明は、(i) 100重量部のポリ−L乳酸(A−α−1成分)に対して、0.001〜3重量部のホスホノ脂肪酸エステル(B成分)を含有する組成物−1および100重量部のポリ−D乳酸(A−α−2成分)に対して、0.001〜3重量部のホスホノ脂肪酸エステル(B成分)を含有する組成物−2を、組成物−1および組成物−2の合計100重量部に対して、0.01〜5重量部のリン酸エステル金属塩(C成分)の存在下、溶融混練してステレオコンプレックスポリ乳酸(A−α―3成分)を調製する工程、並びに
(ii) 得られたステレオコンプレックスポリ乳酸5〜95wt%とメタクリル系樹脂(A−β成分)95〜5wt%からなる樹脂成分100重量部に対し、0.001〜2重量部のホスホノ脂肪酸エステル(B成分)、0.001〜2重量部の、ホスファイト系化合物、ホスホナイト系化合物、ヒンダートフェノール系化合物、チオエーテル系化合物からなる群より選ばれる少なくとも一種の酸化防止剤(D成分)、並びに0.001〜10重量部の末端封鎖剤(E成分)を溶融混練する工程、
からなる前記組成物の製造方法である。
また本発明は該組成物からなる成形品を包含する。
Moreover, this invention is (1) Composition-1 containing 0.001-3 weight part phosphono fatty acid ester (B component) with respect to 100 weight part poly-L lactic acid (A-alpha-1 component). And composition-2 containing 0.001 to 3 parts by weight of phosphono fatty acid ester (component B) with respect to 100 parts by weight of poly-D lactic acid (component A-α-2) Stereocomplex polylactic acid (A-α-3 component) by melting and kneading in the presence of 0.01 to 5 parts by weight of a phosphate ester metal salt (C component) with respect to 100 parts by weight of the total composition-2 And (ii) 0.001-2 weight per 100 parts by weight of the resin component consisting of 5-95 wt% of the obtained stereocomplex polylactic acid and 95-5 wt% of methacrylic resin (A-β component) Part of phosphono fatty acid ester (Component B), 0.001 to 2 parts by weight of at least one antioxidant (D component) selected from the group consisting of phosphite compounds, phosphonite compounds, hindered phenol compounds, thioether compounds, and A step of melt-kneading 0.001 to 10 parts by weight of an end-blocking agent (E component);
It is a manufacturing method of the said composition which consists of.
Moreover, this invention includes the molded article which consists of this composition.
本発明のポリ乳酸組成物およびその成形品は、熱安定性、特に湿熱安定性に優れる。また本発明の製造方法によれば、熱安定性、特に湿熱安定性に優れたポリ乳酸組成物を提供することができる。さらにはメタクリル系樹脂とのポリマーアロイにより、湿熱処理後の寸法変化の少ない、優れた組成物を提供できる。 The polylactic acid composition of the present invention and the molded product thereof are excellent in heat stability, particularly wet heat stability. Moreover, according to the manufacturing method of this invention, the polylactic acid composition excellent in heat stability, especially wet heat stability can be provided. Furthermore, the polymer composition with a methacrylic resin can provide an excellent composition with little dimensional change after wet heat treatment.
〈ポリ乳酸:A−α成分〉
ポリ乳酸(A−α成分)は、主としてL−乳酸単位からなるポリ−L乳酸(A−α―1成分)、主としてD−乳酸単位からなるポリ−D乳酸(A−α―2成分)またはこれらの混合物である。
<Polylactic acid: A-α component>
Polylactic acid (A-α component) is composed mainly of poly-L lactic acid (A-α-1 component) mainly composed of L-lactic acid units, poly-D lactic acid (A-α-2 component) mainly composed of D-lactic acid units, or It is a mixture of these.
ポリ−L乳酸(A−α―1成分)は、主として下記式(4)で表されるL−乳酸単位からなる。A−α−1成分は、好ましくは90〜100モル%のL−乳酸単位および0〜10モル%のL−乳酸以外の共重合単位からなる。 Poly-L lactic acid (A-α-1 component) is mainly composed of L-lactic acid units represented by the following formula (4). The A-α-1 component preferably comprises 90 to 100 mol% of L-lactic acid units and 0 to 10 mol% of copolymerized units other than L-lactic acid.
ポリ−D乳酸(A−α―2成分)は、主として下記式(4)で表されるD−乳酸単位からなる。A−α−2成分は、好ましくは90〜100モル%のD−乳酸単位および0〜10モル%のD−乳酸以外の共重合単位からなる。 Poly-D lactic acid (A-α-2 component) is mainly composed of D-lactic acid units represented by the following formula (4). The A-α-2 component is preferably composed of 90 to 100 mol% of D-lactic acid units and 0 to 10 mol% of copolymerized units other than D-lactic acid.
ポリ−L乳酸(A−α―1成分)もしくはポリ−D乳酸(A−α―2成分)の光学純度は、90〜100モル%であることが好ましい。光学純度がこれより低いと、ポリ乳酸の結晶性や融点が低下し、高い耐熱性が得られにくい。このため、ポリ−L乳酸(A−α―1成分)もしくはポリ−D乳酸(A−α―2成分)の融点は、好ましくは160℃以上、より好ましくは170℃以上、さらに好ましくは175℃以上である。 The optical purity of poly-L lactic acid (A-α-1 component) or poly-D lactic acid (A-α-2 component) is preferably 90 to 100 mol%. If the optical purity is lower than this, the crystallinity and melting point of polylactic acid are lowered, and it is difficult to obtain high heat resistance. Therefore, the melting point of poly-L lactic acid (A-α-1 component) or poly-D lactic acid (A-α-2 component) is preferably 160 ° C. or higher, more preferably 170 ° C. or higher, more preferably 175 ° C. That's it.
かかる観点において、ポリマー原料の乳酸、ラクチドの光学純度は、好ましくは96〜100モル%、より好ましくは97.5〜100モル%、さらに好ましくは98.5〜100モル%、とりわけ好ましくは99〜100モル%の範囲である。 In this respect, the optical purity of lactic acid and lactide of the polymer raw material is preferably 96 to 100 mol%, more preferably 97.5 to 100 mol%, still more preferably 98.5 to 100 mol%, and particularly preferably 99 to 100 mol%. The range is 100 mol%.
共重合単位としては、ポリ−L乳酸(A−α―1成分)であればD−乳酸単位、ポリ−D乳酸(A−α―2成分)であればL−乳酸単位であり、乳酸以外の単位も挙げられる。
乳酸単位以外の共重合単位は、0〜10モル%、好ましくは0〜5モル%、より好ましくは0〜2モル%、さらに好ましくは0〜1モル%の範囲である。
As copolymerized units, poly-L lactic acid (A-α-1 component) is D-lactic acid unit, and poly-D lactic acid (A-α-2 component) is L-lactic acid unit. Other than lactic acid Are also included.
The copolymer unit other than the lactic acid unit is in the range of 0 to 10 mol%, preferably 0 to 5 mol%, more preferably 0 to 2 mol%, still more preferably 0 to 1 mol%.
共重合単位は、2個以上のエステル結合形成可能な官能基を持つジカルボン酸、多価アルコール、ヒドロキシカルボン酸、ラクトン等由来の単位およびこれら種々の構成成分からなる各種ポリエステル、各種ポリエーテル、各種ポリカーボネート等由来の単位が例示される。 Copolymerized units include units derived from dicarboxylic acids, polyhydric alcohols, hydroxycarboxylic acids, lactones and the like having functional groups capable of forming two or more ester bonds, and various polyesters, various polyethers, various types composed of these various components. Examples are units derived from polycarbonate and the like.
ジカルボン酸としては、コハク酸、アジピン酸、アゼライン酸、セバシン酸、テレフタル酸、イソフタル酸等が挙げられる。多価アルコールとしてはエチレングリコール、プロピレングリコール、ブタンジオール、ペンタンジオール、ヘキサンジオール、オクタンジオール、グリセリン、ソルビタン、ネオペンチルグリコール、ジエチレングリコール、トリエチレングリコール、ポリエチレングリコール、ポリプロピレングリコール等の脂肪族多価アルコール類あるいはビスフェノールにエチレンオキシドが付加させたもの等の芳香族多価アルコール等が挙げられる。ヒドロキシカルボン酸として、グリコール酸、ヒドロキシ酪酸等が挙げられる。ラクトンとしては、グリコリド、ε−カプロラクトン、β−プロピオラクトン、δ−ブチロラクトン、β−またはγ−ブチロラクトン、ピバロラクトン、δ−バレロラクトン等が挙げられる。 Examples of the dicarboxylic acid include succinic acid, adipic acid, azelaic acid, sebacic acid, terephthalic acid, and isophthalic acid. Examples of the polyhydric alcohol include aliphatic polyhydric alcohols such as ethylene glycol, propylene glycol, butanediol, pentanediol, hexanediol, octanediol, glycerin, sorbitan, neopentyl glycol, diethylene glycol, triethylene glycol, polyethylene glycol, and polypropylene glycol. Or aromatic polyhydric alcohols, such as what added ethylene oxide to bisphenol, etc. are mentioned. Examples of the hydroxycarboxylic acid include glycolic acid and hydroxybutyric acid. Examples of the lactone include glycolide, ε-caprolactone, β-propiolactone, δ-butyrolactone, β- or γ-butyrolactone, pivalolactone, and δ-valerolactone.
ポリL−乳酸(A−α―1成分)およびポリD−乳酸(A−α―2成分)の重量平均分子量は、本発明の組成物の機械物性および成形性を両立させるため、好ましくは8万〜30万、より好ましくは10万〜25万、さらに好ましくは12〜23万の範囲である。
ポリ乳酸の重量平均分子量および数平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)により測定し標準ポリスチレンに換算した値である。
The weight average molecular weight of poly L-lactic acid (A-α-1 component) and poly D-lactic acid (A-α-2 component) is preferably 8 in order to achieve both the mechanical properties and moldability of the composition of the present invention. The range is from 10,000 to 300,000, more preferably from 100,000 to 250,000, and even more preferably from 1 to 230,000.
The weight average molecular weight and number average molecular weight of polylactic acid are values measured by gel permeation chromatography (GPC) and converted to standard polystyrene.
ポリL−乳酸(A−α―1成分)およびポリD−乳酸(A−α―2成分)の製造方法は、とりわけ限定はなく、従来公知の方法で製造することができ、例えば、L−またはD−ラクチドの溶融開環重合法、低分子量のポリ乳酸の固相重合法、さらに、乳酸を脱水縮合させる直接重合法等を例示することができる。 The production method of poly L-lactic acid (A-α-1 component) and poly D-lactic acid (A-α-2 component) is not particularly limited, and can be produced by a conventionally known method. Examples thereof include a melt ring-opening polymerization method of D-lactide, a solid phase polymerization method of low molecular weight polylactic acid, and a direct polymerization method of dehydrating condensation of lactic acid.
重合反応は、従来公知の反応装置で実施可能であり、例えばヘリカルリボン翼等高粘度用攪拌翼を備えた縦型反応器あるいは横型反応器を単独、または並列にて使用することができる。また、回分式あるいは連続式あるいは半回分式のいずれでも良いし、これらを組み合わせてもよい。 The polymerization reaction can be carried out in a conventionally known reaction apparatus. For example, a vertical reactor or a horizontal reactor equipped with a high-viscosity stirring blade such as a helical ribbon blade can be used alone or in parallel. Moreover, any of a batch type, a continuous type, a semibatch type may be sufficient, and these may be combined.
固相重合法では、プレポリマーは予め結晶化させることが、ペレットの融着防止、生産効率の面から好ましく、固定された縦型或いは横型反応容器、またはタンブラーやキルンの様に容器自身が回転する反応容器(ロータリーキルン等)中、プレポリマーのガラス転移温度以上融点未満の温度範囲の一定温度あるいは重合の進行に伴い次第に昇温させ重合を行う。生成する水を効率的に除去する目的で前記反応容器類の内部を減圧することや、加熱された不活性ガス気流を流通する方法も好適に併用される。 In the solid-state polymerization method, it is preferable to crystallize the prepolymer in advance from the viewpoint of preventing fusion of pellets and production efficiency, and the container itself rotates like a fixed vertical or horizontal reaction vessel, or a tumbler or kiln. In a reaction vessel (such as a rotary kiln), the polymerization is carried out by raising the temperature gradually with the progress of the polymerization at a constant temperature in the temperature range from the glass transition temperature of the prepolymer to less than the melting point. For the purpose of efficiently removing generated water, a method of reducing the pressure inside the reaction vessels and a method of circulating a heated inert gas stream are also preferably used in combination.
本発明の組成物は、ポリ乳酸を製造する際に用いる金属触媒を含有する。金属触媒は、アルカリ土類金属、希土類金属、第三周期の遷移金属、アルミニウム、ゲルマニウム、スズ、およびアンチモンからなる群から選ばれる少なくとも一種の金属元素を含む化合物である。アルカリ土類金属として、マグネシウム、カルシウム、ストロンチウム等が挙げられる。希土類元素として、スカンジウム、イットリウム、ランタン、セリウム等が挙げられる。第三周期の遷移金属として、鉄、コバルト、ニッケル、亜鉛が挙げられる。金属触媒は、例えばこれらの金属のカルボン酸塩、アルコキシド、アリールオキシド、或いはβ−ジケトンのエノラート等として組成物に添加される。重合活性や色相を考慮した場合、オクチル酸スズ、チタンテトライソプロポキシド、アルミニウムトリイソプロポキシドが特に好ましい。 The composition of this invention contains the metal catalyst used when manufacturing polylactic acid. The metal catalyst is a compound containing at least one metal element selected from the group consisting of alkaline earth metals, rare earth metals, third-period transition metals, aluminum, germanium, tin, and antimony. Examples of the alkaline earth metal include magnesium, calcium, and strontium. Examples of rare earth elements include scandium, yttrium, lanthanum, and cerium. As the transition metal of the third period, iron, cobalt, nickel, and zinc can be cited. Metal catalysts are added to the composition, for example, as carboxylates, alkoxides, aryloxides or enolates of β-diketones of these metals. In view of polymerization activity and hue, tin octylate, titanium tetraisopropoxide, and aluminum triisopropoxide are particularly preferable.
金属触媒の含有量は、100重量部のポリ乳酸に対して、好ましくは0.001〜1重量部、より好ましくは、0.005〜0.1重量部である。金属触媒の含有量が少なすぎると重合速度が著しく低化する。逆に多すぎると反応熱による着色、或いは解重合やエステル交換反応が加速されるため、得られる組成物の色相と熱安定性が悪化する。 The content of the metal catalyst is preferably 0.001 to 1 part by weight, more preferably 0.005 to 0.1 part by weight with respect to 100 parts by weight of polylactic acid. When the content of the metal catalyst is too small, the polymerization rate is remarkably lowered. On the contrary, if the amount is too large, coloring due to reaction heat or depolymerization or transesterification reaction is accelerated, so that the hue and thermal stability of the resulting composition are deteriorated.
重合開始剤としてアルコールを用いてもよい。かかるアルコールとしては、ポリ乳酸の重合を阻害せず不揮発性であることが好ましく、例えばデカノール、ドデカノール、テトラデカノール、ヘキサデカノール、オクタデカノール等を好適に用いることができる。 Alcohol may be used as a polymerization initiator. Such alcohol is preferably non-volatile without inhibiting the polymerization of polylactic acid. For example, decanol, dodecanol, tetradecanol, hexadecanol, octadecanol and the like can be suitably used.
〈ステレオコンプレックスポリ乳酸〉
ポリ乳酸は、ステレオコンプレックス結晶を含有することが好ましい。このステレオコンプレックス結晶を含有しているポリ乳酸を、ステレオコンプレックスポリ乳酸という。ステレオコンプレックス結晶は、ポリL−乳酸(A−α―1成分)とポリD−乳酸(A−α―2成分)を混合することにより形成される。この場合、ポリL−乳酸(A−α―1成分)とポリD−乳酸(A−α―2成分)との重量比は、好ましくは90:10〜10:90、より好ましくは75:25〜25:75、さらに好ましくは60:40〜40:60である。
<Stereo complex polylactic acid>
The polylactic acid preferably contains a stereocomplex crystal. Polylactic acid containing this stereocomplex crystal is called stereocomplex polylactic acid. A stereocomplex crystal is formed by mixing poly L-lactic acid (A-α-1 component) and poly D-lactic acid (A-α-2 component). In this case, the weight ratio of poly L-lactic acid (A-α-1 component) to poly D-lactic acid (A-α-2 component) is preferably 90:10 to 10:90, more preferably 75:25. -25: 75, more preferably 60: 40-40: 60.
ポリ乳酸(A―α成分)は、主としてL−乳酸単位からなるポリ−L乳酸(A−α―1成分)および主としてD−乳酸単位からなるポリ−D乳酸(A−α―2成分)を含有し、A−α―1成分とA−α−2成分との重量比が10:90〜90:10の範囲にあることが好ましい。この場合、ポリ−L乳酸(A−α―1成分)はL−乳酸単位を90モル%以上含有し、ポリ−D乳酸(A−α−2成分)はD−乳酸単位を90モル%以上含有することが好ましい。 Polylactic acid (A-α component) consists of poly-L lactic acid (A-α-1 component) mainly composed of L-lactic acid units and poly-D lactic acid (A-α-2 component) mainly composed of D-lactic acid units. And the weight ratio of the A-α-1 component and the A-α-2 component is preferably in the range of 10:90 to 90:10. In this case, poly-L lactic acid (A-α-1 component) contains 90 mol% or more of L-lactic acid units, and poly-D lactic acid (A-α-2 component) contains 90 mol% or more of D-lactic acid units. It is preferable to contain.
高度にステレオコンプレックス化されたステレオコンプレックスポリ乳酸は、示差走査熱量計(DSC)測定の昇温過程における融解ピークのうち195℃以上の割合が80%以上となる。 Highly stereocomplexed stereocomplex polylactic acid has a ratio of 195 ° C. or higher of the melting peak in the temperature rising process of differential scanning calorimeter (DSC) measurement of 80% or higher.
ステレオコンプレックスポリ乳酸の融解ピークは、好ましくは200℃以上、より好ましくは205℃以上、さらに好ましくは210℃以上である。ステレオコンプレックスポリ乳酸の融解ピークが195℃より低いと、その結晶性や融点の低さから耐熱性は不十分である。 The melting peak of stereocomplex polylactic acid is preferably 200 ° C. or higher, more preferably 205 ° C. or higher, and further preferably 210 ° C. or higher. When the melting peak of stereocomplex polylactic acid is lower than 195 ° C., heat resistance is insufficient due to its crystallinity and low melting point.
ステレオコンプレックスポリ乳酸の融解ピークのうち195℃以上の割合は、好ましくは80%以上、より好ましくは90%以上、最も好ましいのは100%である。195℃以上の融解ピークの割合が80%より低いとポリ−L乳酸やポリ−D乳酸に由来するホモ結晶の特徴が表れてしまい、耐熱性が不十分となる。 The ratio of 195 ° C. or higher of the melting peak of stereocomplex polylactic acid is preferably 80% or higher, more preferably 90% or higher, and most preferably 100%. If the ratio of the melting peak at 195 ° C. or higher is lower than 80%, the characteristics of the homocrystal derived from poly-L lactic acid or poly-D lactic acid appear, and the heat resistance becomes insufficient.
かかる高度にステレオコンプレックス化されたステレオコンプレックスポリ乳酸は、ポリL−乳酸(A−α−1成分)とポリD‐乳酸(A−α−2成分)とが、かかる量比で存在することにより、13C−NMRで求めたエナンチオマー平均連鎖長を好適に10から40の範囲とすることができ、ホモ相ポリ乳酸の結晶融解ピークが存在しないで、ステレオコンプレックス相ポリ乳酸の結晶融解ピークのみが観測されるようになる。 Such a highly stereocomplexed stereocomplex polylactic acid has poly L-lactic acid (A-α-1 component) and poly D-lactic acid (A-α-2 component) in such a quantitative ratio. The average enantiomeric chain length determined by 13C-NMR can be preferably in the range of 10 to 40, and only the crystal melting peak of the stereocomplex phase polylactic acid is observed without the crystal melting peak of the homophase polylactic acid. Will come to be.
ここにおいて13C−NMRで求めたエナンチオマー平均連鎖長(Li)は、ポリ乳酸のCH炭素の4連子構造のピークをMakromol.Chem.,191,2287(1990)したがい帰属、その面積比(Iiii,Iisi,Isii,Iiis,Isis,Issi,Iiss,Iss)により式(IV)で定義される値である。iはアイソタクチック(LL、DD)、sはシンジオタクチック(LD、DL)連結を表す。
Li=(3Iiii+2Iisi+2Isii+2Iiis+Isis+Issi+Iiss)/(Iisi+Iiis+Isii+2Isis+2Issi+2Iiss+3Isss)+1
(IV)
Here, the enantiomeric average chain length (Li) determined by 13C-NMR is the peak of the quadruple structure of CH carbon of polylactic acid. Chem. , 191, 287 (1990), and the area ratio (Iiii, Iisi, Isi, Iiis, Isis, Issi, Iiss, Isss) is a value defined by the formula (IV). i represents isotactic (LL, DD), and s represents syndiotactic (LD, DL) linkage.
Li = (3Iiii + 2Iisi + 2Isi + 2Iii + Isis + Issi + Iiss) / (Iisi + Iis + Isi + 2Isis + 2Issi + 2Iiss + 3Isss) +1
(IV)
本発明においては、エナンチオマー平均連鎖長(Li)が、10から40の範囲にあることが好ましく、かかる条件を満たすことにより、組成物の耐熱性、とりわけ好適な離型性を達成することができる。 In the present invention, the enantiomeric average chain length (Li) is preferably in the range of 10 to 40, and by satisfying such a condition, the heat resistance of the composition, particularly suitable release properties can be achieved. .
エナンチオマー平均連鎖長が10に満たないと、DSC測定において、ステレオコンプレックス相ポリ乳酸が高度に形成されていても、組成物の耐熱性に劣ることがあり、40を超えていると、ステレオコンプレックスポリ乳酸の形成性に劣りさらに耐熱性が劣ることがあるためである。かかる観点に加え、さらに組成物の離型性の観点よりエナンチオマー平均連鎖長は好ましくは15から40、より好ましくは18から39の範囲が好適に選択される。 If the average enantiomeric chain length is less than 10, even if a stereocomplex phase polylactic acid is highly formed in the DSC measurement, the composition may be inferior in heat resistance. This is because the formation of lactic acid is inferior and the heat resistance is inferior. In addition to this point of view, the enantiomeric average chain length is preferably selected from the range of 15 to 40, more preferably 18 to 39, from the viewpoint of the releasability of the composition.
〈メタクリル系樹脂:A−β成分〉
本発明におけるメタクリル系樹脂(A−β成分)とは、メタクリル酸メチル成分単位を主成分、好ましくは70%以上含むものであればよく、他のビニル系単量体成分単位を好ましくは30%以下、より好ましくは20%以下共重合した共重合体でもよい。その他のビニル系単量体としては、α−メチルスチレン、o−メチルスチレン、p−メチルスチレン、o−エチルスチレン、p−エチルスチレン、p−t−ブチルスチレンなどの芳香族ビニル系単量体、アクリロニトリル、メタクリロニトリル、エタクリロニトリルなどのシアン化ビニル系単量体、イタコン酸グリシジル、アリルグリシジルエーテル、スチレン−p−グリシジルエーテル、p−グリシジルスチレン、マレイン酸無水物、マレイン酸モノエチルエステル、イタコン酸、イタコン酸無水物、グルタル酸無水物、N−メチルマレイミド、N−エチルマレイミド、N−シクロヘキシルマレイミド、N−フェニルマレイミドなどのN−置換マレイミド、アクリルアミド、メタクリルアミド、N−メチルアクリルアミド、ブトキシメチルアクリルアミド、N−プロピルメタクリルアミド、アクリル酸、アクリル酸メチル、アクリル酸エチル、アクリル酸ブチル、アクリル酸シクロヘキシル、アクリル酸アミノエチル、アクリル酸プロピルアミノエチル、アクリル酸2−ヒドロキシエチル、アクリル酸2−ヒドロキシプロピル、アクリル酸グリシジル、アクリル酸ジシクロペンテニルオキシエチル、アクリル酸ジシクロペンタニル、ジアクリル酸ブタンジオール、ジアクリル酸ノナンジオール、ジアクリル酸ポリエチレングリコール、2−(ヒドロキシメチル)アクリル酸メチル、2−(ヒドロキシメチル)アクリル酸エチル、メタクリル酸、メタクリル酸エチル、メタクリル酸ブチル、メタクリル酸シクロへキシル、メタクリル酸ジメチルアミノエチル、メタクリル酸エチルアミノプロピル、メタクリル酸フェニルアミノエチル、メタクリル酸シクロヘキシルアミノエチル、メタクリル酸2−ヒドロキシエチル、メタクリル酸2−ヒドロキシプロピル、メタクリル酸グリシジル、メタクリル酸ジシクロペンテニルオキシエチル、メタクリル酸ジシクロペンタニル、メタクリル酸ペンタメチルピペリジル、メタクリル酸テトラメチルピペリジル、メタクリル酸ベンジル、ジメタクリル酸エチレングリコール、ジメタクリル酸プロピレングリコール、ジメタクリル酸ポリエチレングリコール、N−ビニルジエチルアミン、N−アセチルビニルアミン、アリルアミン、メタアリルアミン、N−メチルアリルアミン、p−アミノスチレン、2−イソプロペニル−オキサゾリン、2−ビニル−オキサゾリン、2−アクロイル−オキサゾリンおよび2−スチリル−オキサゾリンなどが挙げられ、これらのビニル系単量体は単独または2種以上を用いることができる。また、耐熱性、低吸湿性、表面硬度の点で、ラクトン環、マレイン酸無水物、グルタル酸無水物などの環構造単位を主鎖に含有する共重合体が好ましい。さらに、環構造を主鎖に含有する共重合体を用いる場合には、環構造を含有しないメタクリル系樹脂を併用することがより好ましい。
<Methacrylic resin: A-β component>
The methacrylic resin (A-β component) in the present invention may be one containing a methyl methacrylate component unit as a main component, preferably 70% or more, and preferably 30% of other vinyl monomer component units. Hereinafter, a copolymer obtained by copolymerization of 20% or less is more preferable. Other vinyl monomers include aromatic vinyl monomers such as α-methylstyrene, o-methylstyrene, p-methylstyrene, o-ethylstyrene, p-ethylstyrene, and pt-butylstyrene. , Vinyl cyanide monomers such as acrylonitrile, methacrylonitrile, ethacrylonitrile, glycidyl itaconate, allyl glycidyl ether, styrene-p-glycidyl ether, p-glycidyl styrene, maleic anhydride, monoethyl maleate N-substituted maleimides such as itaconic acid, itaconic anhydride, glutaric anhydride, N-methylmaleimide, N-ethylmaleimide, N-cyclohexylmaleimide, N-phenylmaleimide, acrylamide, methacrylamide, N-methylacrylamide, Butoxymethyl Kurylamide, N-propylmethacrylamide, acrylic acid, methyl acrylate, ethyl acrylate, butyl acrylate, cyclohexyl acrylate, aminoethyl acrylate, propylaminoethyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxy acrylate Propyl, glycidyl acrylate, dicyclopentenyloxyethyl acrylate, dicyclopentanyl acrylate, butanediol diacrylate, nonanediol diacrylate, polyethylene glycol diacrylate, methyl 2- (hydroxymethyl) acrylate, 2- (hydroxy Methyl) ethyl acrylate, methacrylic acid, ethyl methacrylate, butyl methacrylate, cyclohexyl methacrylate, dimethylaminoethyl methacrylate, ethylamino methacrylate Nopropyl, phenylaminoethyl methacrylate, cyclohexylaminoethyl methacrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, glycidyl methacrylate, dicyclopentenyloxyethyl methacrylate, dicyclopentanyl methacrylate, pentamethacrylate Methylpiperidyl, tetramethylpiperidyl methacrylate, benzyl methacrylate, ethylene glycol dimethacrylate, propylene glycol dimethacrylate, polyethylene glycol dimethacrylate, N-vinyldiethylamine, N-acetylvinylamine, allylamine, methallylamine, N-methyl Allylamine, p-aminostyrene, 2-isopropenyl-oxazoline, 2-vinyl-oxazoline, 2-acryloyl-oxy Gelsolin and 2-styryl - and oxazoline. These vinyl monomers may be used alone or in combination. From the viewpoints of heat resistance, low hygroscopicity, and surface hardness, a copolymer containing a ring structural unit such as a lactone ring, maleic anhydride, glutaric anhydride, etc. in the main chain is preferred. Furthermore, when a copolymer containing a ring structure in the main chain is used, it is more preferable to use a methacrylic resin not containing a ring structure.
本発明で用いられるメタクリル系樹脂(A−β成分)としては、メタクリル系樹脂の少なくとも1種が、重量平均分子量5万〜45万かつガラス転移温度が100℃以上のメタクリル系樹脂である。このような条件を満たすメタクリル系樹脂を用いることで、ポリ乳酸樹脂との分子間相互作用が増大し親和性が向上するため、湿熱処理後の寸法保持性に優れた樹脂組成物を得ることができる。 As the methacrylic resin (A-β component) used in the present invention, at least one methacrylic resin is a methacrylic resin having a weight average molecular weight of 50,000 to 450,000 and a glass transition temperature of 100 ° C. or higher. By using a methacrylic resin that satisfies these conditions, the intermolecular interaction with the polylactic acid resin is increased and the affinity is improved, so that it is possible to obtain a resin composition having excellent dimensional retention after wet heat treatment. it can.
本発明で用いられるメタクリル系樹脂(A−β成分)としては、耐熱性および流動性の点で、メタクリル系樹脂の少なくとも1種が、重量平均分子量7万〜20万であることが好ましく、9万〜15万がより好ましい。ここでいう重量平均分子量とは、溶媒としてヘキサフルオロイソプロパノールを用いたGPCで測定した標準ポリスチレンに換算した値である。 As the methacrylic resin (A-β component) used in the present invention, at least one methacrylic resin preferably has a weight average molecular weight of 70,000 to 200,000 in view of heat resistance and fluidity. 10,000 to 150,000 are more preferable. The weight average molecular weight here is a value converted to standard polystyrene measured by GPC using hexafluoroisopropanol as a solvent.
本発明で用いられるメタクリル系樹脂(A−β成分)としては、耐熱性の点で、(B)メタクリル系樹脂の少なくとも1種が、ガラス転移温度が80℃以上が好ましく、90℃以上がより好ましく、100℃以上がさらに好ましい。上限は特に限定されないが、流動性の点で、150℃以下が好ましい。ここでいうガラス転移温度は、JIS K7121に記載されている方法に準じて測定した値であり、DSC測定により、20℃/分で昇温した時の中間点ガラス転移温度である。本発明においては、メタクリル系樹脂(A−β成分)として、ガラス転移温度が100℃以上であるメタクリル系樹脂を少なくとも1種含むものであることが好ましい。 As the methacrylic resin (A-β component) used in the present invention, at least one of (B) methacrylic resin is preferable in terms of heat resistance, glass transition temperature is preferably 80 ° C. or higher, more preferably 90 ° C. or higher. Preferably, 100 degreeC or more is more preferable. Although an upper limit is not specifically limited, 150 degreeC or less is preferable at the point of fluidity | liquidity. The glass transition temperature here is a value measured according to the method described in JIS K7121, and is the midpoint glass transition temperature when the temperature is raised at 20 ° C./min by DSC measurement. In the present invention, the methacrylic resin (A-β component) preferably contains at least one methacrylic resin having a glass transition temperature of 100 ° C. or higher.
メタクリル系樹脂のガラス転移温度を制御する方法として、特に制限があるわけではないが、メタクリル系樹脂の立体構造を制御する方法が挙げられる。一例として、シンジオタクチシチー45%以上のものや、ヘテロタクチシチーが45%以下であるものが用いられることが、ガラス転移温度で見た耐熱性の観点から、一般的に用いられている。ここでいうシンジオタクチシチー、ヘテロタクチシチー、アイソタクチシチーとは、溶媒として、重水素化クロロホルムを用いた1H−NMR測定において、0.9ppm、1.0ppm、1.2ppmに観察される直鎖分岐のメチル基のピークの積分強度の合計を100%として、それぞれのピークの積分強度の割合を百分率で表した値である。 The method for controlling the glass transition temperature of the methacrylic resin is not particularly limited, but a method for controlling the three-dimensional structure of the methacrylic resin can be mentioned. As an example, a material having a syndiotacticity of 45% or more or a material having a heterotacticity of 45% or less is generally used from the viewpoint of heat resistance as viewed from the glass transition temperature. As used herein, syndiotacticity, heterotacticity, and isotacticity are those directly observed at 0.9 ppm, 1.0 ppm, and 1.2 ppm in 1H-NMR measurement using deuterated chloroform as a solvent. The total integrated intensity of the peaks of chain-branched methyl groups is 100%, and the ratio of the integrated intensity of each peak is expressed as a percentage.
本発明で用いられるメタクリル系樹脂(A−β成分)としては、流動性の点で、メルトボリュームフローレート(MVR、ISO1133、240℃、2.16kg)の値として、0.5〜80cm3/10分のものが好ましい。1〜70cm3/10分のものを用いると、成形品外観の優れた樹脂組成物となるためより好ましく、2〜60cm3/10分のものが特に好ましい。 As the methacrylic resin (A-β component) used in the present invention, in terms of fluidity, the melt volume flow rate (MVR, ISO 1133, 240 ° C., 2.16 kg) has a value of 0.5 to 80 cm 3 / 10 minutes is preferred. With those 1~70cm 3/10 min, preferably from for an excellent resin composition molded article appearance, particularly preferably from 2~60cm 3/10 min.
かかるメタクリル系樹脂(A−β成分)とポリ乳酸(A−α成分)の重量比(A−β/A−α)は、5/95〜95/5、好ましくは10/90〜50/50、さらに好ましくは15/85〜40/60の範囲が選択される。メタクリル系樹脂(A−β成分)とポリ乳酸(A−α成分)の含有比が5/95より小さくなるとメタクリル系樹脂を配合することによる良好な湿熱処理後の寸法安定性が付与できず、95/5より大きくなると、地球環境保護の目的の観点から好ましくない。 The weight ratio (A-β / A-α) between the methacrylic resin (A-β component) and polylactic acid (A-α component) is 5/95 to 95/5, preferably 10/90 to 50/50. More preferably, the range of 15/85 to 40/60 is selected. When the content ratio of the methacrylic resin (A-β component) and the polylactic acid (A-α component) is less than 5/95, dimensional stability after wet heat treatment cannot be imparted by blending the methacrylic resin, If it exceeds 95/5, it is not preferable from the viewpoint of the purpose of protecting the global environment.
〈ホスホノ脂肪酸エステル:B成分〉
本発明の組成物は、ポリ乳酸(A−α成分)の金属触媒の失活剤としてホスホノ脂肪酸エステル(B成分)を含有する。ホスホノ脂肪酸エステル(B成分)は、ホスホン酸ジエステル部位とカルボン酸エステル部位が脂肪族炭化水素基を介して結合した化合物で、無色透明で耐熱性に優れるため得られる組成物の色相は良好となる。特に下記一般式(1)で表されるホスホノ脂肪酸エステルが好ましい。
<Phosphono fatty acid ester: B component>
The composition of the present invention contains a phosphono fatty acid ester (component B) as a metal catalyst deactivator for polylactic acid (component A-α). A phosphono fatty acid ester (component B) is a compound in which a phosphonic acid diester moiety and a carboxylic acid ester moiety are bonded via an aliphatic hydrocarbon group, and since it is colorless and transparent and excellent in heat resistance, the hue of the composition obtained is good. . Particularly preferred are phosphono fatty acid esters represented by the following general formula (1).
式中R1〜R3はそれぞれ独立に、炭素数1〜20のアルキル基または炭素数6〜12のアリール基である。炭素数1〜20のアルキル基として、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基等が挙げられる。炭素数6〜12のアリール基として、フェニル基、ナフタレン−イル基が挙げられる。R1〜R3は、これらが全て同一であっても、異なるものがあっても構わない。またnは1〜3の整数である。 In the formula, R 1 to R 3 are each independently an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 12 carbon atoms. Examples of the alkyl group having 1 to 20 carbon atoms include an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. Examples of the aryl group having 6 to 12 carbon atoms include a phenyl group and a naphthalenyl group. R 1 to R 3 may be the same or different from each other. N is an integer of 1 to 3.
式(1)で表される化合物として、ジエチルホスホノ酢酸エチル、ジ−n−プロピルホスホノ酢酸エチル、ジ−n−ブチルホスホノ酢酸エチル、ジ−n−ヘキシルホスホノ酢酸エチル、ジ−n−オクチルホスホノ酢酸エチル、ジ−n−デシルホスホノ酢酸エチル、ジ−n−ドデシルホスホノ酢酸エチル、ジ−n−オクタデシルホスホノ酢酸エチル、ジフェニルホスホノ酢酸エチル、ジエチルホスホノ酢酸デシル、ジエチルホスホノ酢酸ドデシル、ジエチルホスホノ酢酸オクタデシル、ジエチルホスホノプロピオン酸エチル、ジ−n−プロピルホスホノプロピオン酸エチル、ジ−n−ブチルホスホノプロピオン酸エチル、ジ−n−ヘキシルホスホノプロピオン酸エチル、ジ−n−オクチルホスホノプロピオン酸エチル、ジ−n−デシルホスホノプロピオン酸エチル、ジ−n−ドデシルホスホノプロピオン酸エチル、ジ−n−オクタデシルホスホノプロピオン酸エチル、ジフェニルホスホノプロピオン酸エチル、ジエチルホスホノプロピオン酸デシル、ジエチルホスホノプロピオン酸ドデシル、ジエチルホスホノプロピオン酸オクタデシル、ジエチルホスホノ酪酸エチル、ジ−n−プロピルホスホノ酪酸エチル、ジ−n−ブチルホスホノ酪酸エチル、ジ−n−ヘキシルホスホノ酪酸エチル、ジ−n−オクチルホスホノ酪酸エチル、ジ−n−デシルホスホノ酪酸エチル、ジ−n−ドデシルホスホノ酪酸エチル、ジ−n−オクタデシルホスホノ酪酸エチル、ジフェニルホスホノ酪酸エチル、ジエチルホスホノ酪酸デシル、ジエチルホスホノ酪酸ドデシル、ジエチルホスホノ酪酸オクタデシルが挙げられる。効能や取扱いの容易さを考慮すると、ジエチルホスホノ酢酸エチル、ジ−n−プロピルホスホノ酢酸エチル、ジ−n−ブチルホスホノ酢酸エチル、ジ−n−ヘキシルホスホノ酢酸エチル、ジエチルホスホノ酢酸デシル、ジエチルホスホノ酢酸オクタデシル等が挙げられる。 As the compound represented by the formula (1), ethyl diethylphosphonoacetate, di-n-propylphosphonoacetate ethyl, di-n-butylphosphonoacetate ethyl, di-n-hexylphosphonoacetate ethyl, di-n-octyl Ethyl phosphonoacetate, ethyl di-n-decylphosphonoacetate, ethyl di-n-dodecylphosphonoacetate, ethyl di-n-octadecylphosphonoacetate, ethyl diphenylphosphonoacetate, decyl diethylphosphonoacetate, dodecyl diethylphosphonoacetate , Octadecyl diethylphosphonoacetate, ethyl diethylphosphonopropionate, ethyl di-n-propylphosphonopropionate, ethyl di-n-butylphosphonopropionate, ethyl di-n-hexylphosphonopropionate, di-n -Ethyl octylphosphonopropionate, di-n-decylphosphono Ethyl lopionate, ethyl di-n-dodecylphosphonopropionate, ethyl di-n-octadecylphosphonopropionate, ethyl diphenylphosphonopropionate, decyl diethylphosphonopropionate, dodecyl diethylphosphonopropionate, diethylphosphono Octadecyl propionate, ethyl diethylphosphonobutyrate, ethyl di-n-propylphosphonobutyrate, ethyl di-n-butylphosphonobutyrate, ethyl di-n-hexylphosphonobutyrate, ethyl di-n-octylphosphonobutyrate, di- Ethyl n-decylphosphonobutyrate, ethyl di-n-dodecylphosphonobutyrate, ethyl di-n-octadecylphosphonobutyrate, ethyl diphenylphosphonobutyrate, decyl diethylphosphonobutyrate, dodecyl diethylphosphonobutyrate, octadecyl diethylphosphonobutyrate And the like. In view of efficacy and ease of handling, ethyl diethylphosphonoacetate, ethyl di-n-propylphosphonoacetate, ethyl di-n-butylphosphonoacetate, ethyl di-n-hexylphosphonoacetate, decyl diethylphosphonoacetate, Examples thereof include octadecyl diethylphosphonoacetate.
式(1)において、R1〜R3の炭素数が20以下であると、その融点がポリ乳酸や組成物の製造温度よりも低くなるため十分に融解混合し、効率的に金属触媒を補足することができる。またホスホノ脂肪酸エステル(B成分)は、ホスホン酸ジエステル部位とカルボン酸エステル部位の間に脂肪族炭化水素基を有する。ポリ乳酸中の金属触媒を効率的に捕捉するためには式(1)において、nが1〜3の整数であることが好ましい。 In the formula (1), when the carbon number of R 1 to R 3 is 20 or less, the melting point becomes lower than the production temperature of polylactic acid or the composition, so that the mixture is sufficiently melted and mixed, and the metal catalyst is efficiently captured. can do. The phosphono fatty acid ester (component B) has an aliphatic hydrocarbon group between the phosphonic acid diester moiety and the carboxylic acid ester moiety. In order to efficiently capture the metal catalyst in the polylactic acid, in the formula (1), n is preferably an integer of 1 to 3.
ホスホノ脂肪酸エステル(B成分)の含有量は、樹脂成分(A成分)100重量部に対して0.001〜5重量部、好ましくは0.005〜2重量部である。ホスホノ脂肪酸エステルの含有量が、少なすぎると残留する金属触媒の失活効率が極めて悪く、十分な効果が得られない。また、多すぎると成形加工時に使用する金型の汚染が著しくなる。 Content of phosphono fatty acid ester (B component) is 0.001-5 weight part with respect to 100 weight part of resin components (A component), Preferably it is 0.005-2 weight part. If the content of the phosphono fatty acid ester is too small, the deactivation efficiency of the remaining metal catalyst is extremely poor and a sufficient effect cannot be obtained. On the other hand, when the amount is too large, contamination of the mold used at the time of molding processing becomes significant.
ホスホノ脂肪酸エステル(B成分)は、重合終了時に添加するのが通例であるが、B成分は、リン酸エステル金属塩(C成分)に対しても失活作用があり、B成分によるC成分の熱安定性の悪化が顕著な場合には、重合終了時における所定量のB成分を全て添加するよりは、重合終了時と、その後、押出、成形の各プロセスにおいて、他の成分と混練する際に分けて添加することが好ましい。 The phosphono fatty acid ester (component B) is usually added at the end of the polymerization, but the component B also has a deactivating effect on the phosphate ester metal salt (component C). When deterioration of thermal stability is remarkable, rather than adding all of the predetermined amount of component B at the end of polymerization, at the end of polymerization and then when kneading with other components in each process of extrusion and molding It is preferable to add in portions.
押出、成形の各プロセスにおけるホスホノ脂肪酸エステル(B成分)の添加量は、L−乳酸(A−α−1成分)とD−乳酸(A−α−2成分)の各々100重量部に対して0.001〜2重量部、好ましくは0.005〜1重量部である。B成分の添加量が少なすぎると、金属触媒を失活する効果が得られない。また、多すぎるB成分による金型の汚染が著しくなる。 The amount of phosphono fatty acid ester (component B) added in each process of extrusion and molding is 100 parts by weight of L-lactic acid (A-α-1 component) and D-lactic acid (A-α-2 component). 0.001 to 2 parts by weight, preferably 0.005 to 1 part by weight. When there is too little addition amount of B component, the effect which deactivates a metal catalyst will not be acquired. Further, the contamination of the mold due to too much B component becomes significant.
〈リン酸エステル金属塩:C成分〉
リン酸エステル金属塩(C成分)としては、下記一般式(2)または(3)で示される化合物が挙げられる。
<Phosphate metal salt: Component C>
Examples of the phosphoric ester metal salt (component C) include compounds represented by the following general formula (2) or (3).
式中R1は、水素原子または炭素数1〜4のアルキル基である。炭素数1〜4のアルキル基として、メチル基、プロピル基、ブチル基等が挙げられる。R2およびR3はそれぞれ独立に、水素原子または炭素数1〜12のアルキル基である。炭素数1〜12のアルキル基として、メチル基、プロピル基、ブチル基、へキシル基、デシル基等が挙げられる。M1はアルカリ金属原子、アルカリ土類金属原子、亜鉛原子またはアルミニウム原子である。アルカリ金属原子として、ナトリウム、カリウム等が挙げられる。アルカリ土類金属原子として、マグネシウム、カルシウム、リチウム等が挙げられる。pは1または2である。qはM1がアルカリ金属原子、アルカリ土類金属原子または亜鉛原子のときは0、アルミニウム原子のときは1または2である。 In the formula, R 1 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, a propyl group, and a butyl group. R 2 and R 3 are each independently a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, a propyl group, a butyl group, a hexyl group, and a decyl group. M 1 is an alkali metal atom, an alkaline earth metal atom, a zinc atom or an aluminum atom. Examples of the alkali metal atom include sodium and potassium. Examples of the alkaline earth metal atom include magnesium, calcium, and lithium. p is 1 or 2. q is 0 when M 1 is an alkali metal atom, alkaline earth metal atom or zinc atom, and is 1 or 2 when M 1 is an aluminum atom.
式中R4、R5はそれぞれ独立に、水素原子または炭素数1〜12のアルキル基である。炭素数1〜12のアルキル基として、メチル基、プロピル基、ブチル基、へキシル基、デシル基等が挙げられる。M2はアルカリ金属原子、アルカリ土類金属原子、亜鉛原子またはアルミニウム原子である。アルカリ金属原子として、ナトリウム、カリウム等が挙げられる。アルカリ土類金属原子として、マグネシウム、カルシウム、リチウム等が挙げられる。pは1または2である。qはM2がアルカリ金属原子、アルカリ土類金属原子または亜鉛原子のときは0を、アルミニウム原子のときは1または2である。 In the formula, R 4 and R 5 are each independently a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. Examples of the alkyl group having 1 to 12 carbon atoms include a methyl group, a propyl group, a butyl group, a hexyl group, and a decyl group. M 2 is an alkali metal atom, an alkaline earth metal atom, a zinc atom or an aluminum atom. Examples of the alkali metal atom include sodium and potassium. Examples of the alkaline earth metal atom include magnesium, calcium, and lithium. p is 1 or 2. q is 0 when M 2 is an alkali metal atom, alkaline earth metal atom or zinc atom, and is 1 or 2 when M 2 is an aluminum atom.
リン酸エステル金属塩(C成分)としては、ナトリウム−2,2’−メチレンビス(4,6−ジ−t−ブチルフェニル)ホスフェート、アルミニウムビス(2,2’−メチレンビス−4,6−ジ−t−ブチルフェニルホスフェート)等が挙げられる。 Examples of phosphate metal salts (component C) include sodium-2,2′-methylenebis (4,6-di-t-butylphenyl) phosphate, aluminum bis (2,2′-methylenebis-4,6-di-). t-butylphenyl phosphate) and the like.
式(2)または(3)で表されるリン酸エステル金属塩のM1、M2は、Na、K、Al、Mg、Ca、Liが好ましく、特に、K、Na、Al、LiなかでもLi、Alが最も好適に用いることができる。なかでもADEKA(株)製の商品名、アデカスタブNA−10、NA−11、NA−21、NA−30、NA−35、NA−71等が好適な剤として例示される。 M 1 and M 2 of the phosphoric acid ester metal salt represented by the formula (2) or (3) are preferably Na, K, Al, Mg, Ca, Li, and particularly, among K, Na, Al, and Li. Li and Al can be most preferably used. Among them, trade names manufactured by ADEKA Co., Ltd., ADK STAB NA-10, NA-11, NA-21, NA-30, NA-35, NA-71 and the like are exemplified as suitable agents.
リン酸エステル金属塩(C成分)の含有量は、樹脂成分(A成分)100重量部に対し、0.01〜5重量部、好ましくは0.01〜1重量部、より好ましくは0.01〜0.5重量部、さらに好ましくは0.02〜0.3重量部である。少なすぎる場合には、ステレオ化度を向上する効果が小さく、多すぎるとコンプレックス相結晶融点を低下させるので好ましくない。 The content of the phosphoric ester metal salt (component C) is 0.01 to 5 parts by weight, preferably 0.01 to 1 part by weight, more preferably 0.01 to 100 parts by weight of the resin component (component A). It is -0.5 weight part, More preferably, it is 0.02-0.3 weight part. When the amount is too small, the effect of improving the degree of stereoization is small, and when too large, the complex phase crystal melting point is lowered, which is not preferable.
〈酸化防止剤:D成分〉
酸化防止剤(D成分)は、ホスファイト系化合物、ホスホナイト系化合物、ヒンダートフェノール系化合物およびチオエーテル系化合物からなる群より選ばれる少なくとも一種である。酸化防止剤(D成分)は、ホスファイト系化合物およびヒンダードフェノール系化合物の二種からなることが、末端封鎖剤由来の悪臭や悪臭原因物質と思われる由来の金型汚染を低減させる観点で特に好ましい。
<Antioxidant: D component>
The antioxidant (component D) is at least one selected from the group consisting of phosphite compounds, phosphonite compounds, hindered phenol compounds, and thioether compounds. Antioxidant (component D) is composed of two types of phosphite compounds and hindered phenol compounds, from the viewpoint of reducing mold contamination derived from terminal blocker-derived malodor and odor-causing substances. Particularly preferred.
(ホスファイト系化合物)
ホスファイト系化合物として、トリフェニルホスファイト、トリス(ノニルフェニル)ホスファイト、トリデシルホスファイト、トリオクチルホスファイト、トリオクタデシルホスファイト、ジデシルモノフェニルホスファイト、ジオクチルモノフェニルホスファイト、ジイソプロピルモノフェニルホスファイト、モノブチルジフェニルホスファイト、モノデシルジフェニルホスファイト、モノオクチルジフェニルホスファイト、トリス(ジエチルフェニル)ホスファイト、トリス(ジ−iso−プロピルフェニル)ホスファイト、トリス(ジ−n−ブチルフェニル)ホスファイト、トリス(2,4−ジ−tert−ブチルフェニル)ホスファイト、トリス(2,6−ジ−tert−ブチルフェニル)ホスファイト、ジステアリルペンタエリスリトールジホスファイト、ビス(2,4−ジ−tert−ブチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,6−ジ−tert−ブチル−4−メチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,6−ジ−tert−ブチル−4−エチルフェニル)ペンタエリスリトールジホスファイト、ビス{2,4−ビス(1−メチル−1−フェニルエチル)フェニル}ペンタエリスリトールジホスファイト、フェニルビスフェノールAペンタエリスリトールジホスファイト、ビス(ノニルフェニル)ペンタエリスリトールジホスファイト、およびジシクロヘキシルペンタエリスリトールジホスファイト等が挙げられる。
(Phosphite compounds)
As phosphite compounds, triphenyl phosphite, tris (nonylphenyl) phosphite, tridecyl phosphite, trioctyl phosphite, trioctadecyl phosphite, didecyl monophenyl phosphite, dioctyl monophenyl phosphite, diisopropyl monophenyl Phosphite, monobutyl diphenyl phosphite, monodecyl diphenyl phosphite, monooctyl diphenyl phosphite, tris (diethylphenyl) phosphite, tris (di-iso-propylphenyl) phosphite, tris (di-n-butylphenyl) Phosphite, tris (2,4-di-tert-butylphenyl) phosphite, tris (2,6-di-tert-butylphenyl) phosphite, distearyl pentaeri Ritol diphosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, bis ( 2,6-di-tert-butyl-4-ethylphenyl) pentaerythritol diphosphite, bis {2,4-bis (1-methyl-1-phenylethyl) phenyl} pentaerythritol diphosphite, phenylbisphenol A penta Examples include erythritol diphosphite, bis (nonylphenyl) pentaerythritol diphosphite, and dicyclohexyl pentaerythritol diphosphite.
さらに他のホスファイト系化合物としては二価フェノール類と反応し環状構造を有するものも使用できる。例えば、2,2’−メチレンビス(4,6−ジ−tert−ブチルフェニル)(2,4−ジ−tert−ブチルフェニル)ホスファイト、2,2’−メチレンビス(4,6−ジ−tert−ブチルフェニル)(2−tert−ブチル−4−メチルフェニル)ホスファイト、および2,2−メチレンビス(4,6−ジ−tert−ブチルフェニル)オクチルホスファイト等が挙げられる。 Furthermore, as other phosphite compounds, those that react with dihydric phenols and have a cyclic structure can be used. For example, 2,2′-methylenebis (4,6-di-tert-butylphenyl) (2,4-di-tert-butylphenyl) phosphite, 2,2′-methylenebis (4,6-di-tert- Butylphenyl) (2-tert-butyl-4-methylphenyl) phosphite, 2,2-methylenebis (4,6-di-tert-butylphenyl) octyl phosphite, and the like.
好適なホスファイト系化合物は、ジステアリルペンタエリスリトールジホスファイト、ビス(2,4−ジ−tert−ブチルフェニル)ペンタエリスリトールジホスファイト、ビス(2,6−ジ−tert−ブチル−4−メチルフェニル)ペンタエリスリトールジホスファイト、およびビス{2,4−ビス(1−メチル−1−フェニルエチル)フェニル}ペンタエリスリトールジホスファイトである。 Suitable phosphite compounds are distearyl pentaerythritol diphosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methyl). Phenyl) pentaerythritol diphosphite, and bis {2,4-bis (1-methyl-1-phenylethyl) phenyl} pentaerythritol diphosphite.
(ホスホナイト系化合物)
ホスホナイト化合物として、テトラキス(2,4−ジ−tert−ブチルフェニル)−4,4’−ビフェニレンジホスホナイト、テトラキス(2,4−ジ−tert−ブチルフェニル)−4,3’−ビフェニレンジホスホナイト、テトラキス(2,4−ジ−tert−ブチルフェニル)−3,3’−ビフェニレンジホスホナイト、テトラキス(2,6−ジ−tert−ブチルフェニル)−4,4’−ビフェニレンジホスホナイト、テトラキス(2,6−ジ−tert−ブチルフェニル)−4,3’−ビフェニレンジホスホナイト、テトラキス(2,6−ジ−tert−ブチルフェニル)−3,3’−ビフェニレンジホスホナイト、ビス(2,4−ジ−tert−ブチルフェニル)−4−フェニル−フェニルホスホナイト、ビス(2,4−ジ−tert−ブチルフェニル)−3−フェニル−フェニルホスホナイト、ビス(2,6−ジ−n−ブチルフェニル)−3−フェニル−フェニルホスホナイト、ビス(2,6−ジ−tert−ブチルフェニル)−4−フェニル−フェニルホスホナイト、ビス(2,6−ジ−tert−ブチルフェニル)−3−フェニル−フェニルホスホナイト等が挙げられる。テトラキス(ジ−tert−ブチルフェニル)−ビフェニレンジホスホナイト、ビス(ジ−tert−ブチルフェニル)−フェニル−フェニルホスホナイトが好ましく、テトラキス(2,4−ジ−tert−ブチルフェニル)−ビフェニレンジホスホナイト、ビス(2,4−ジ−tert−ブチルフェニル)−フェニル−フェニルホスホナイトがより好ましい。かかるホスホナイト化合物は上記アルキル基が2以上置換したアリール基を有するホスファイト化合物との併用可能であり好ましい。
(Phosphonite compounds)
Examples of phosphonite compounds include tetrakis (2,4-di-tert-butylphenyl) -4,4′-biphenylene diphosphonite, tetrakis (2,4-di-tert-butylphenyl) -4,3′-biphenylene diphospho. Knight, tetrakis (2,4-di-tert-butylphenyl) -3,3'-biphenylenediphosphonite, tetrakis (2,6-di-tert-butylphenyl) -4,4'-biphenylenediphosphonite, Tetrakis (2,6-di-tert-butylphenyl) -4,3′-biphenylenediphosphonite, tetrakis (2,6-di-tert-butylphenyl) -3,3′-biphenylenediphosphonite, bis ( 2,4-di-tert-butylphenyl) -4-phenyl-phenylphosphonite, bis (2,4-di-tert Butylphenyl) -3-phenyl-phenylphosphonite, bis (2,6-di-n-butylphenyl) -3-phenyl-phenylphosphonite, bis (2,6-di-tert-butylphenyl) -4- Examples thereof include phenyl-phenylphosphonite, bis (2,6-di-tert-butylphenyl) -3-phenyl-phenylphosphonite. Tetrakis (di-tert-butylphenyl) -biphenylene diphosphonite, bis (di-tert-butylphenyl) -phenyl-phenylphosphonite are preferred, and tetrakis (2,4-di-tert-butylphenyl) -biphenylene diphospho Knight and bis (2,4-di-tert-butylphenyl) -phenyl-phenylphosphonite are more preferred. Such a phosphonite compound is preferable because it can be used in combination with a phosphite compound having an aryl group in which two or more alkyl groups are substituted.
ホスホナイト化合物としてはテトラキス(2,4−ジ−tert−ブチルフェニル)−ビフェニレンジホスホナイトが好ましく、該ホスホナイトを主成分とする安定剤は、Sandostab P−EPQ(商標、Clariant社製)およびIrgafos P−EPQ(商標、CIBA SPECIALTY CHEMICALS社製)として市販されておりいずれも利用できる。 The phosphonite compound is preferably tetrakis (2,4-di-tert-butylphenyl) -biphenylenediphosphonite, and stabilizers based on the phosphonite are Sandostab P-EPQ (trademark, manufactured by Clariant) and Irgafos P. -It is commercially available as EPQ (trademark, manufactured by CIBA SPECIALTY CHEMICALS) and any of them can be used.
(ヒンダードフェノール系化合物)
ヒンダードフェノール化合物としては、通常樹脂に配合される各種の化合物が使用できる。かかるヒンダードフェノール化合物としては、α−トコフェロール、ブチルヒドロキシトルエン、シナピルアルコール、ビタミンE、オクタデシル−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート、2−tert−ブチル−6−(3’−tert−ブチル−5’−メチル−2’−ヒドロキシベンジル)−4−メチルフェニルアクリレート、2,6−ジ−tert−ブチル−4−(N,N−ジメチルアミノメチル)フェノール、3,5−ジ−tert−ブチル−4−ヒドロキシベンジルホスホネートジエチルエステル、2,2’−メチレンビス(4−メチル−6−tert−ブチルフェノール)、2,2’−メチレンビス(4−エチル−6−tert−ブチルフェノール)、4,4’−メチレンビス(2,6−ジ−tert−ブチルフェノール)、2,2’−メチレンビス(4−メチル−6−シクロヘキシルフェノール)、2,2’−ジメチレン−ビス(6−α−メチル−ベンジル−p−クレゾール)、2,2’−エチリデン−ビス(4,6−ジ−tert−ブチルフェノール)、2,2’−ブチリデン−ビス(4−メチル−6−tert−ブチルフェノール)、4,4’−ブチリデンビス(3−メチル−6−tert−ブチルフェノール)、トリエチレングリコール−N−ビス−3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオネート、1,6−へキサンジオールビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、ビス[2−tert−ブチル−4−メチル6−(3−tert−ブチル−5−メチル−2−ヒドロキシベンジル)フェニル]テレフタレート、3,9−ビス{2−[3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオニルオキシ]−1,1,−ジメチルエチル}−2,4,8,10−テトラオキサスピロ[5,5]ウンデカン、4,4’−チオビス(6−tert−ブチル−m−クレゾール)、4,4’−チオビス(3−メチル−6−tert−ブチルフェノール)、2,2’−チオビス(4−メチル−6−tert−ブチルフェノール)、ビス(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)スルフィド、4,4’−ジ−チオビス(2,6−ジ−tert−ブチルフェノール)、4,4’−トリ−チオビス(2,6−ジ−tert−ブチルフェノール)、2,2−チオジエチレンビス−[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]、2,4−ビス(n−オクチルチオ)−6−(4−ヒドロキシ−3,5−ジ−tert−ブチルアニリノ)−1,3,5−トリアジン、N,N’−ヘキサメチレンビス−(3,5−ジ−tert−ブチル−4−ヒドロキシヒドロシンナミド)、N,N’−ビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオニル]ヒドラジン、1,1,3−トリス(2−メチル−4−ヒドロキシ−5−tert−ブチルフェニル)ブタン、1,3,5−トリメチル−2,4,6−トリス(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)ベンゼン、トリス(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)イソシアヌレート、トリス(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)イソシアヌレート、1,3,5−トリス(4−tert−ブチル−3−ヒドロキシ−2,6−ジメチルベンジル)イソシアヌレート、1,3,5−トリス2[3(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオニルオキシ]エチルイソシアヌレート、テトラキス[メチレン−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート]メタン、トリエチレングリコール−N−ビス−3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオネート、トリエチレングリコール−N−ビス−3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)アセテート、3,9−ビス[2−{3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)アセチルオキシ}−1,1−ジメチルエチル]−2,4,8,10−テトラオキサスピロ[5,5]ウンデカン、テトラキス[メチレン−3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオネート]メタン、1,3,5−トリメチル−2,4,6−トリス(3−tert−ブチル−4−ヒドロキシ−5−メチルベンジル)ベンゼン、およびトリス(3−tert−ブチル−4−ヒドロキシ−5−メチルベンジル)イソシアヌレート等が例示される。
(Hindered phenolic compounds)
As the hindered phenol compound, various compounds usually blended in a resin can be used. Examples of such hindered phenol compounds include α-tocopherol, butylhydroxytoluene, sinapyl alcohol, vitamin E, octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate, 2-tert-butyl. -6- (3'-tert-butyl-5'-methyl-2'-hydroxybenzyl) -4-methylphenyl acrylate, 2,6-di-tert-butyl-4- (N, N-dimethylaminomethyl) Phenol, 3,5-di-tert-butyl-4-hydroxybenzylphosphonate diethyl ester, 2,2′-methylenebis (4-methyl-6-tert-butylphenol), 2,2′-methylenebis (4-ethyl-6) -Tert-butylphenol), 4,4'-methylenebis (2,6-di-t) rt-butylphenol), 2,2′-methylenebis (4-methyl-6-cyclohexylphenol), 2,2′-dimethylene-bis (6-α-methyl-benzyl-p-cresol), 2,2′-ethylidene -Bis (4,6-di-tert-butylphenol), 2,2'-butylidene-bis (4-methyl-6-tert-butylphenol), 4,4'-butylidenebis (3-methyl-6-tert-butylphenol) ), Triethylene glycol-N-bis-3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate, 1,6-hexanediol bis [3- (3,5-di-tert- Butyl-4-hydroxyphenyl) propionate], bis [2-tert-butyl-4-methyl 6- (3-tert-butyl-5) Methyl-2-hydroxybenzyl) phenyl] terephthalate, 3,9-bis {2- [3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy] -1,1, -dimethylethyl} -2,4,8,10-tetraoxaspiro [5,5] undecane, 4,4'-thiobis (6-tert-butyl-m-cresol), 4,4'-thiobis (3-methyl-6- tert-butylphenol), 2,2′-thiobis (4-methyl-6-tert-butylphenol), bis (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, 4,4′-di-thiobis (2,6-di-tert-butylphenol), 4,4′-tri-thiobis (2,6-di-tert-butylphenol), 2,2-thiodiethylenebi -[3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 2,4-bis (n-octylthio) -6- (4-hydroxy-3,5-di-tert-butylanilino ) -1,3,5-triazine, N, N′-hexamethylenebis- (3,5-di-tert-butyl-4-hydroxyhydrocinnamide), N, N′-bis [3- (3 5-di-tert-butyl-4-hydroxyphenyl) propionyl] hydrazine, 1,1,3-tris (2-methyl-4-hydroxy-5-tert-butylphenyl) butane, 1,3,5-trimethyl- 2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) benzene, tris (3,5-di-tert-butyl-4-hydroxyphenyl) isocyanurate , Tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate 1,3,5-tris 2 [3 (3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxy] ethyl isocyanurate, tetrakis [methylene-3- (3,5-di-tert-butyl -4-hydroxyphenyl) propionate] methane, triethylene glycol-N-bis-3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate, triethylene glycol-N-bis-3- (3 -Tert-butyl-4-hydroxy-5-methylphenyl) acetate, 3,9-bis [2- {3- 3-tert-butyl-4-hydroxy-5-methylphenyl) acetyloxy} -1,1-dimethylethyl] -2,4,8,10-tetraoxaspiro [5,5] undecane, tetrakis [methylene-3 -(3-tert-butyl-4-hydroxy-5-methylphenyl) propionate] methane, 1,3,5-trimethyl-2,4,6-tris (3-tert-butyl-4-hydroxy-5-methyl Examples include benzyl) benzene and tris (3-tert-butyl-4-hydroxy-5-methylbenzyl) isocyanurate.
上記化合物の中でも、本発明においてはテトラキス[メチレン−3−(3−tert−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオネート]メタン、オクタデシル−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピオネート、および3,9−ビス[2−{3−(3−t−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオニルオキシ}−1,1−ジメチルエチル]−2,4,8,10−テトラオキサスピロ[5,5]ウンデカンが好ましく利用される。特に3,9−ビス[2−{3−(3−t−ブチル−4−ヒドロキシ−5−メチルフェニル)プロピオニルオキシ}−1,1−ジメチルエチル]−2,4,8,10−テトラオキサスピロ[5,5]ウンデカンが好ましい。上記ヒンダードフェノール系化合物は、単独でまたは2種以上を組み合わせて使用することができる。 Among the above compounds, tetrakis [methylene-3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionate] methane, octadecyl-3- (3,5-di-tert-butyl-) is used in the present invention. 4-hydroxyphenyl) propionate, and 3,9-bis [2- {3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy} -1,1-dimethylethyl] -2,4 , 8,10-Tetraoxaspiro [5,5] undecane is preferably used. In particular, 3,9-bis [2- {3- (3-tert-butyl-4-hydroxy-5-methylphenyl) propionyloxy} -1,1-dimethylethyl] -2,4,8,10-tetraoxa Spiro [5,5] undecane is preferred. The said hindered phenol type compound can be used individually or in combination of 2 or more types.
(チオエーテル系化合物)
チオエーテル系化合物の具体例として、ジラウリルチオジプロピオネート、ジトリデシルチオジプロピオネート、ジミリスチルチオジプロピオネート、ジステアリルチオジプロピオネート、ペンタエリスリトール−テトラキス(3−ラウリルチオプロピオネート)、ペンタエリスリトール−テトラキス(3−ドデシルチオプロピオネート)、ペンタエリスリトール−テトラキス(3−オクタデシルチオプロピオネート)、ペンタエリスリトールテトラキス(3−ミリスチルチオプロピオネート)、ペンタエリスリトール−テトラキス(3−ステアリルチオプロピオネート)等が挙げられる。
(Thioether compounds)
Specific examples of thioether compounds include dilauryl thiodipropionate, ditridecyl thiodipropionate, dimyristyl thiodipropionate, distearyl thiodipropionate, pentaerythritol-tetrakis (3-lauryl thiopropionate), Pentaerythritol-tetrakis (3-dodecylthiopropionate), pentaerythritol-tetrakis (3-octadecylthiopropionate), pentaerythritol tetrakis (3-myristylthiopropionate), pentaerythritol-tetrakis (3-stearylthio) Propionate) and the like.
酸化防止剤(D成分)の含有量は、樹脂成分(A成分)100重量部に対し、0.001〜2重量部であり、好ましくは0.005〜1重量部、より好ましくは0.01〜0.5重量部である。かかる配合量が0.001重量部より少ない場合は酸化防止効果が不足するため滞留熱安定性が低下し、2重量部を超えると、かえって酸化防止効果が低下するばかりか、酸化防止剤由来の揮発分による金型汚染が目立ち、好ましくない。 The content of the antioxidant (component D) is 0.001 to 2 parts by weight, preferably 0.005 to 1 part by weight, more preferably 0.01 to 100 parts by weight of the resin component (component A). -0.5 parts by weight. When the blending amount is less than 0.001 part by weight, the anti-oxidation effect is insufficient, so the residence heat stability is lowered. When it exceeds 2 parts by weight, not only the antioxidant effect is lowered, but also the antioxidant-derived effect is derived. Mold contamination due to volatile matter is conspicuous and is not preferable.
また、前記リン系安定剤とヒンダードフェノール系安定剤を組み合わせて使用することが好ましい。リン系安定剤とヒンダードフェノール系安定剤を組み合わせて使用することで、安定剤としての相乗効果が発揮され、より成形時の色相悪化を抑制できる。 Moreover, it is preferable to use the phosphorus stabilizer and the hindered phenol stabilizer in combination. By using a combination of a phosphorus-based stabilizer and a hindered phenol-based stabilizer, a synergistic effect as a stabilizer is exhibited, and the deterioration of hue during molding can be further suppressed.
〈末端封鎖剤:E成分〉
本発明の組成物は末端封鎖剤(E成分)を含有する。末端封鎖剤(E成分)は、カルボジイミド化合物、エポキシ化合物、オキサゾリン化合物およびオキサジン化合物からなる群より選ばれる少なくとも一種であることが好ましい。
<End blocker: E component>
The composition of this invention contains terminal blocker (E component). The terminal blocking agent (component E) is preferably at least one selected from the group consisting of carbodiimide compounds, epoxy compounds, oxazoline compounds and oxazine compounds.
(カルボジイミド化合物)
カルボジイミド化合物としては以下の化合物が例示される。例えば、ジシクロヘキシルカルボジイミド、ジイソプロピルカルボジイミド、ジイソブイチルカルボジイミド、ジオクチルカルボジイミド、オクチルデシルカルボジイミド、ジ−t−ブチルカルボジイミド、ジベンジルカルボジイミド、ジフェニルカルボジイミド、N−オクタデシル−N’−フェニルカルボジイミド、N−ベンジル−N’−フェニルカルボジイミド、N−ベンジル−N’−トリルカルボジイミド、ジ−o−トルイルカルボジイミド、ジ−p−トルイルカルボジイミド、ビス(p−アミノフェニル)カルボジイミド、ビス(p−クロロフェニル)カルボジイミド、ビス(o−クロロフェニル)カルボジイミド、ビス(o−エチルフェニル)カルボジイミド、ビス(p−エチルフェニル)カルボジイミドビス(o−イソプロピルフェニル)カルボジイミド、ビス(p−イソプロピルフェニル)カルボジイミド、ビス(o−イソブチルフェニル)カルボジイミド、ビス(p−イソブチルフェニル)カルボジイミド、ビス(2,5−ジクロロフェニル)カルボジイミド、ビス(2,6−ジメチルフェニル)カルボジイミド、ビス(2,6−ジエチルフェニル)カルボジイミド、ビス(2−エチル−6−イソプロピルフェニル)カルボジイミド、ビス(2−ブチル−6−イソプロピルフェニル)カルボジイミド、ビス(2,6−ジイソプロピルフェニル)カルボジイミド、ビス(2,6−ジ−t−ブチルフェニル)カルボジイミド、ビス(2,4,6−トリメチルフェニル)カルボジイミド、ビス(2,4,6−トリイソプロピルフェニル)カルボジイミド、ビス(2,4,6−トリブチルフェニル)カルボジイミド、ジβナフチルカルボシイミド、N−トリル−N’−シクロヘキシルカルボシイミド、N−トリル−N’−フェニルカルボシイミド、p−フェニレンビス(o−トルイルカルボジイミド)、p−フェニレンビス(シクロヘキシルカルボジイミド、p−フェニレンンビス(p−クロロフェニルカルボジイミド)、2,6,2’,6’−テトライソプロピルジフェニルカルボジイミド、ヘキサメチレンビス(シクロヘキシルカルボジイミド)、エチレンビス(フェニルカルボジイミド)、エチレンビス(シクロヘキシルカルボジイミド)、などのモノまたはポリカルボジイミド化合物が例示される。
(Carbodiimide compound)
Examples of the carbodiimide compound include the following compounds. For example, dicyclohexylcarbodiimide, diisopropylcarbodiimide, diisobutylcarbodiimide, dioctylcarbodiimide, octyldecylcarbodiimide, di-t-butylcarbodiimide, dibenzylcarbodiimide, diphenylcarbodiimide, N-octadecyl-N'-phenylcarbodiimide, N-benzyl-N'- Phenylcarbodiimide, N-benzyl-N'-tolylcarbodiimide, di-o-toluylcarbodiimide, di-p-toluylcarbodiimide, bis (p-aminophenyl) carbodiimide, bis (p-chlorophenyl) carbodiimide, bis (o-chlorophenyl) Carbodiimide, bis (o-ethylphenyl) carbodiimide, bis (p-ethylphenyl) carbodiimide bis (o-isopropylphenol) Lu) carbodiimide, bis (p-isopropylphenyl) carbodiimide, bis (o-isobutylphenyl) carbodiimide, bis (p-isobutylphenyl) carbodiimide, bis (2,5-dichlorophenyl) carbodiimide, bis (2,6-dimethylphenyl) Carbodiimide, bis (2,6-diethylphenyl) carbodiimide, bis (2-ethyl-6-isopropylphenyl) carbodiimide, bis (2-butyl-6-isopropylphenyl) carbodiimide, bis (2,6-diisopropylphenyl) carbodiimide, Bis (2,6-di-t-butylphenyl) carbodiimide, bis (2,4,6-trimethylphenyl) carbodiimide, bis (2,4,6-triisopropylphenyl) carbodiimide, bis (2,4,6- Ributylphenyl) carbodiimide, di-β-naphthylcarbosiimide, N-tolyl-N′-cyclohexylcarbosiimide, N-tolyl-N′-phenylcarbosiimide, p-phenylenebis (o-toluylcarbodiimide), p- Phenylenebis (cyclohexylcarbodiimide, p-phenylenenebis (p-chlorophenylcarbodiimide), 2,6,2 ', 6'-tetraisopropyldiphenylcarbodiimide, hexamethylenebis (cyclohexylcarbodiimide), ethylenebis (phenylcarbodiimide), ethylenebis Examples thereof include mono- or polycarbodiimide compounds such as (cyclohexylcarbodiimide).
なかでも反応性、安定性の観点からビス(2,6−ジイソプロピルフェニル)カルボジイミド、2,6,2’,6’−テトライソプロピルジフェニルカルボジイミドが好ましい。 Of these, bis (2,6-diisopropylphenyl) carbodiimide and 2,6,2 ', 6'-tetraisopropyldiphenylcarbodiimide are preferred from the viewpoints of reactivity and stability.
またこれらのうち工業的に入手可能なジシクロヘキシルカルボジイミド、ビス(2,6−ジイソプロピルフェニル)カルボジイミドが好適に使用できるである。さらに上記ポリカルボジイミド化合物として市販のポリカルボジイミド化合物は、合成する必要もなく好適に使用することができる。かかる市販のポリカルボジイミド化合物としては例えば日清紡(株)より市販されているカルボジライトの商品名で販売されているカルボジライトLA−1、あるいはHMV−8CAなどを例示することができる。本発明の組成物の色調、熱分解性、耐加水分解性などに与える影響より、カルボジイミド化合物が好ましい。 Of these, industrially available dicyclohexylcarbodiimide and bis (2,6-diisopropylphenyl) carbodiimide can be suitably used. Furthermore, a commercially available polycarbodiimide compound as the polycarbodiimide compound can be suitably used without the need for synthesis. Examples of such commercially available polycarbodiimide compounds include Carbodilite LA-1 and HMV-8CA sold under the trade name of Carbodilite sold by Nisshinbo Co., Ltd. A carbodiimide compound is preferred because of its influence on the color tone, thermal decomposability, hydrolysis resistance and the like of the composition of the present invention.
(エポキシ化合物)
エポキシ化合物としては、グリシジルエーテル化合物、グリシジルエステル化合物、グリジジルアミン化合物、グリシジルイミド化合物、グリシジルアミド化合物、脂環式エポキシ化合物を好ましく使用することができる。かかる剤を配合することで、機械的特性、成形性、耐熱性、耐久性に優れたポリ乳酸樹脂組成物および成形品を得ることができる。
(Epoxy compound)
As an epoxy compound, a glycidyl ether compound, a glycidyl ester compound, a glycidyl amine compound, a glycidyl imide compound, a glycidyl amide compound, and an alicyclic epoxy compound can be preferably used. By blending such an agent, a polylactic acid resin composition and a molded product excellent in mechanical properties, moldability, heat resistance, and durability can be obtained.
グリシジルエーテル化合物の例としては例えば、ステアリルグリシジルエーテル、フェニルグリシジルエーテル、エチレンオキシドラウリルアルコールグリシジルエーテル、エチレングリコールジグリシジルエーテル、ポリエチレングルコールジグリシジルエーテル、ポリプロピレングリコールジグリシジルエーテル、ネオペンチレングリコールジグリシジルエーテル、ポリテトラメチレングリコールジグリシジルエーテル、グリセロールトリグリシジルエーテル、トリメチロールプロパントリグリシジルエーテル、ペンタエリスリトールテトラグリシジルエーテル、その他ビス(4−ヒドロキシフェニル)メタンなどのビスフェノール類とエピクロルヒドリンとの縮合反応で得られるビスフェノールAジグリシジルエーテル型エポキシ樹脂などを挙げることができる。なかでもビスフェノールAジグリシジルエーテル型エポキシ樹脂が好ましい。 Examples of glycidyl ether compounds include, for example, stearyl glycidyl ether, phenyl glycidyl ether, ethylene oxide lauryl alcohol glycidyl ether, ethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether, polypropylene glycol diglycidyl ether, neopentylene glycol diglycidyl ether, Bisphenol A obtained by condensation reaction of epichlorohydrin with polytetramethylene glycol diglycidyl ether, glycerol triglycidyl ether, trimethylolpropane triglycidyl ether, pentaerythritol tetraglycidyl ether, and other bisphenols such as bis (4-hydroxyphenyl) methane Diglycidyl ether type epoxy resin Etc. can be mentioned. Of these, bisphenol A diglycidyl ether type epoxy resins are preferred.
グリシジルエステル化合物の例としては例えば安息香酸グリシジルエステル、ステアリン酸グリシジルエステル、パーサティック酸グリシジルエステル、テレフタル酸ジグリシジルエステル、フタル酸ジグリシジルエステル、シクロヘキサンジカルボン酸ジグリシジルエステル、アジピン酸ジグリシジルエステル、コハク酸ジグリシジルエステル、ドデカンジオン酸ジグリシジルエステル、ピロメリット酸テトラグリシジルエステルなどが挙げられる。なかでも安息香酸グリシジルエステル、バーサティック酸グリシジルエステルが好ましい。 Examples of glycidyl ester compounds include glycidyl benzoate, glycidyl stearate, persic acid glycidyl ester, terephthalic acid diglycidyl ester, phthalic acid diglycidyl ester, cyclohexanedicarboxylic acid diglycidyl ester, adipic acid diglycidyl ester, and succinic acid. Examples include acid diglycidyl ester, dodecanedioic acid diglycidyl ester, and pyromellitic acid tetraglycidyl ester. Of these, glycidyl benzoate and glycidyl versatate are preferred.
グリシジルアミン化合物の例としては例えば、テトラグリシジルアミンジフェニルメタン、トリグリシジル−p−アミノフェノール、ジグリシジルアニリン、ジグリシジルトルイジン、テトラグリシジルメタキシレンジアミン、トリグリシジルイソシアヌレート、などが挙げられる。 Examples of the glycidylamine compound include tetraglycidylamine diphenylmethane, triglycidyl-p-aminophenol, diglycidylaniline, diglycidyltoluidine, tetraglycidylmetaxylenediamine, triglycidyl isocyanurate, and the like.
グリシジルイミド、グリシジルアミド化合物の例としては例えば、N−グリシジルフタルイミド、N−グリシジル−4,5−ジメチルフタルイミド、N−グリシジル−3,6−ジメチルフタルイミド、N−グリシジルサクシンイミド、N−グリシジル−1,2,3,4−テトラヒドロフタルイミド、N−グリシジルマレインイミド、N−グリシジルベンズアミド、N−グリシジルステアリルアミドなどが挙げられる。
なかでもN−グリシジルフタルイミドが好ましい。
Examples of glycidylimide and glycidylamide compounds include, for example, N-glycidylphthalimide, N-glycidyl-4,5-dimethylphthalimide, N-glycidyl-3,6-dimethylphthalimide, N-glycidylsuccinimide, N-glycidyl-1 , 2,3,4-tetrahydrophthalimide, N-glycidyl maleimide, N-glycidyl benzamide, N-glycidyl stearyl amide and the like.
Of these, N-glycidylphthalimide is preferable.
脂環式エポキシ化合物の例としては、3,4−エポキシシクロヘキシル−3,4−シクロヘキシルカルボキシレート、ビス(3,4−エポキシシクロヘキシルメチル)アジペート、ビニルシクロヘキセンジエポキシド、N−メチル−4,5−エポキシシクロヘキサン−1,2−ジカルボン酸イミド、N−フェニル−4,5−エポキシシクロヘキサン−1,2−ジカルボン酸イミド、などが挙げられる。 Examples of alicyclic epoxy compounds include 3,4-epoxycyclohexyl-3,4-cyclohexylcarboxylate, bis (3,4-epoxycyclohexylmethyl) adipate, vinylcyclohexene diepoxide, N-methyl-4,5- Examples thereof include epoxycyclohexane-1,2-dicarboxylic imide, N-phenyl-4,5-epoxycyclohexane-1,2-dicarboxylic imide, and the like.
その他のエポキシ化合物としてエポキシ化大豆油、エポキシ化アマニ油、エポキシ化鯨油などのエポキシ変性脂肪酸グリセリド、フェノールノボラック型エポキシ樹脂、クレゾールノボラック型エポキシ樹脂、などを用いることができる。 As other epoxy compounds, epoxy-modified fatty acid glycerides such as epoxidized soybean oil, epoxidized linseed oil, and epoxidized whale oil, phenol novolac type epoxy resins, cresol novolac type epoxy resins, and the like can be used.
(オキサゾリン化合物)
オキサゾリン化合物としては、2−メトキシ−2−オキサゾリン、2−ブトキシ−2−オキサゾリン、2−ステアリルオキシ−2−オキサゾリン、2−シクロヘキシルオキシ−2−オキサゾリン、2−アリルオキシ−2−オキサゾリン、2−ベンジルオキシ−2−オキサゾリン、2−p−フェニルフェノキシ−2−オキサゾリン、2−メチル−2−オキサゾリン、2−シクロヘキシル−2−オキサゾリン、2−メタアリル−2−オキサゾリン、2−クロチルー2−オキサゾリン、2−フェニル−2−オキサゾリン、2−o−エチルフェニル−2−オキサゾリン、2−o−プロピルフェニル−2−オキサゾリン、2−p−フェニルフェニル−2−オキサゾリン、2,2’−ビス(2−オキサゾリン)、2,2’−ビス(4−メチル−2−オキサゾリン)、2,2’−ビス(4−ブチル−2−オキサゾリン)、2,2’−m−フェニレンビス(2−オキサゾリン)、2,2’−p−フェニレンビス(4−メチル−2−オキサゾリン)、2,2’−p−フェニレンビス(4,4’−メチル−2−オキサゾリン)、2,2’−エチレンビス(2−オキサゾリン)、2,2’−テトラメチレンビス(2−オキサゾリン)、2,2’−ヘキサメチレンビス(2−オキサゾリン)、2,2’−エチレンビス(4−メチル−2−オキサゾリン)、2,2’−テトラメチレンビス(4,4’−ジメチル−2−オキサゾリン)、2,2’−シクロヘキシレンビス(2−オキサゾリン)、2,2’−ジフェニレンビス(4−メチル−2−オキサゾリン)などが挙げられる。さらに上記化合物をモノマー単位として含むポリオキサゾリン化合物なども挙げられる。
(Oxazoline compound)
Examples of the oxazoline compound include 2-methoxy-2-oxazoline, 2-butoxy-2-oxazoline, 2-stearyloxy-2-oxazoline, 2-cyclohexyloxy-2-oxazoline, 2-allyloxy-2-oxazoline, 2-benzyl Oxy-2-oxazoline, 2-p-phenylphenoxy-2-oxazoline, 2-methyl-2-oxazoline, 2-cyclohexyl-2-oxazoline, 2-methallyl-2-oxazoline, 2-crotyl-2-oxazoline, 2- Phenyl-2-oxazoline, 2-o-ethylphenyl-2-oxazoline, 2-o-propylphenyl-2-oxazoline, 2-p-phenylphenyl-2-oxazoline, 2,2′-bis (2-oxazoline) 2,2′-bis (4-methyl-2-oxazo ), 2,2'-bis (4-butyl-2-oxazoline), 2,2'-m-phenylenebis (2-oxazoline), 2,2'-p-phenylenebis (4-methyl-2-) Oxazoline), 2,2′-p-phenylenebis (4,4′-methyl-2-oxazoline), 2,2′-ethylenebis (2-oxazoline), 2,2′-tetramethylenebis (2-oxazoline) ), 2,2′-hexamethylenebis (2-oxazoline), 2,2′-ethylenebis (4-methyl-2-oxazoline), 2,2′-tetramethylenebis (4,4′-dimethyl-2) -Oxazoline), 2,2'-cyclohexylenebis (2-oxazoline), 2,2'-diphenylenebis (4-methyl-2-oxazoline) and the like. Furthermore, the polyoxazoline compound etc. which contain the said compound as a monomer unit are mentioned.
(オキサジン化合物)
オキサジン化合物としては、2−メトキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−ヘキシルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−デシルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−シクロヘキシルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−アリルオキシ−5,6−ジヒドロ−4H−1,3−オキサジン、2−クロチルオキシ−5,6−ジヒドロ−4H−1,3−オキサジンなどが挙げられる。
(Oxazine compound)
Examples of the oxazine compound include 2-methoxy-5,6-dihydro-4H-1,3-oxazine, 2-hexyloxy-5,6-dihydro-4H-1,3-oxazine, 2-decyloxy-5,6- Dihydro-4H-1,3-oxazine, 2-cyclohexyloxy-5,6-dihydro-4H-1,3-oxazine, 2-allyloxy-5,6-dihydro-4H-1,3-oxazine, 2-crotyloxy -5,6-dihydro-4H-1,3-oxazine and the like.
さらに2,2’−ビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2’−メチレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2’−エチレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2’−ヘキサメチレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2’−p−フェニレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)、2,2’−P,P’−ジフェニレンビス(5,6−ジヒドロ−4H−1,3−オキサジン)などが挙げられる。さらに上記した化合物をモノマー単位として含むポリオキサジン化合物などが挙げられる。 Further, 2,2′-bis (5,6-dihydro-4H-1,3-oxazine), 2,2′-methylenebis (5,6-dihydro-4H-1,3-oxazine), 2,2′- Ethylenebis (5,6-dihydro-4H-1,3-oxazine), 2,2′-hexamethylenebis (5,6-dihydro-4H-1,3-oxazine), 2,2′-p-phenylene Bis (5,6-dihydro-4H-1,3-oxazine), 2,2′-P, P′-diphenylenebis (5,6-dihydro-4H-1,3-oxazine) and the like can be mentioned. Furthermore, the polyoxazine compound etc. which contain the above-mentioned compound as a monomer unit are mentioned.
上記オキサゾリン化合物やオキサジン化合物のなかでは2,2’−m−フェニレンビス(2−オキサゾリン)や2,2’−p−フェニレンビス(2−オキサゾリン)が好ましいものとして選択される。 Among the oxazoline compounds and oxazine compounds, 2,2'-m-phenylenebis (2-oxazoline) and 2,2'-p-phenylenebis (2-oxazoline) are preferably selected.
末端封鎖剤(E成分)の含有量は、樹脂成分(A成分)100重量部に対して、好ましくは0.001〜10重量部、より好ましくは0.05〜5重量部、さらに好ましくは0.1〜3重量部である。含有量が0.001部未満ではカルボキシル末端に対する末端封鎖剤の添加量が少なすぎ、十分な耐加水分解性が得られず、10重量部を超えるとゲル化などを起こし、流動性が著しく低下するばかりか、末端封鎖剤由来の悪臭や、悪臭原因物質由来と思われる金型汚染が激しくなり、好ましくない。 The content of the terminal blocking agent (component E) is preferably 0.001 to 10 parts by weight, more preferably 0.05 to 5 parts by weight, and still more preferably 0, relative to 100 parts by weight of the resin component (component A). 0.1 to 3 parts by weight. If the content is less than 0.001 part, the amount of the end-capping agent added to the carboxyl terminal is too small, and sufficient hydrolysis resistance cannot be obtained. If the content exceeds 10 parts by weight, gelation occurs and the fluidity is remarkably lowered. In addition, the bad odor derived from the end capping agent and the mold contamination that seems to be derived from the odor-causing substance become severe, which is not preferable.
〈衝撃改質剤:F成分〉
本発明の組成物は衝撃改質剤(F成分)を含有してもよい。衝撃改質剤(F成分)としては、(i)その内部に少なくとも1種以上のゴム層を有し、その成分がアクリル系成分、シリコン系成分、スチレン系成分、ニトリル系成分、共役ジエン系成分、ウレタン系成分、エチレンプロピレン系成分から選ばれる1種以上であり、ゴム層以外の成分がビニル単量体である衝撃改質剤(F−α成分)および(ii)実質的にゴム成分を含まない衝撃改質剤(F−β成分)が挙げられる。これら2種は、単独でも使用してもよく、併用しても良く、各々の種類の中で単数以上の化合物を使用しても構わないことは言うまでもない。その使用は目的に応じて使い分けることが好ましい。
<Impact modifier: F component>
The composition of the present invention may contain an impact modifier (F component). As an impact modifier (F component), (i) it has at least one rubber layer inside, and the component is an acrylic component, silicon component, styrene component, nitrile component, conjugated diene An impact modifier (F-α component) in which at least one component selected from a component, a urethane component, and an ethylene propylene component, and the component other than the rubber layer is a vinyl monomer, and (ii) a substantially rubber component The impact modifier (F-beta component) which does not contain is mentioned. These two types may be used alone or in combination, and it goes without saying that one or more compounds may be used in each type. It is preferable to use it properly according to the purpose.
(F−α成分)
内部に少なくとも1種以上のゴム層を有し、その成分がアクリル系成分、シリコン系成分、スチレン系成分、ニトリル系成分、共役ジエン系成分、ウレタン系成分、エチレンプロピレン系成分から選ばれる1種以上であり、ゴム層以外の成分がビニル単量体である衝撃改質剤(F−α成分)としては、ゴム成分含有量40重量%未満のスチレン単位含有樹脂(F−α−1成分)、ゴム成分含有量40重量%以上のスチレン単位含有樹脂(F−α−2成分)からなる群より選ばれる少なくとも一種の樹脂が好ましい。
(F-α component)
It has at least one rubber layer inside, and the component is selected from an acrylic component, a silicon component, a styrene component, a nitrile component, a conjugated diene component, a urethane component, and an ethylene propylene component. As described above, as the impact modifier (F-α component) in which components other than the rubber layer are vinyl monomers, a styrene unit-containing resin (F-α-1 component) having a rubber component content of less than 40% by weight. At least one resin selected from the group consisting of a styrene unit-containing resin (F-α-2 component) having a rubber component content of 40% by weight or more is preferred.
(F−α−1成分)
ゴム成分含有量が40重量%未満のスチレン単位含有樹脂(F−α−1成分)とは、スチレン系単量体と必要に応じてこれらと共重合可能な他のビニル単量体およびゴム成分よりなる群より選ばれる1種以上を重合して得られる樹脂である。
(F-α-1 component)
The styrene unit-containing resin (F-α-1 component) having a rubber component content of less than 40% by weight is a styrene monomer and, if necessary, other vinyl monomers and rubber components copolymerizable therewith. It is a resin obtained by polymerizing one or more selected from the group consisting of:
スチレン系単量体としては、スチレン、α−メチルスチレン、o−メチルスチレン、p−メチルスチレン、ビニルキシレン、エチルスチレン、ジメチルスチレン、p−tert−ブチルスチレン、ビニルナフタレン、メトキシスチレン、モノブロムスチレン、ジブロムスチレン、フルオロスチレン、トリブロムスチレン等のスチレン誘導体が挙げられる。特にスチレンが好ましい。さらにこれらは単独または2種以上用いることができる。 Styrene monomers include styrene, α-methylstyrene, o-methylstyrene, p-methylstyrene, vinylxylene, ethylstyrene, dimethylstyrene, p-tert-butylstyrene, vinylnaphthalene, methoxystyrene, and monobromostyrene. , Styrene derivatives such as dibromostyrene, fluorostyrene, and tribromostyrene. Styrene is particularly preferable. Furthermore, these can be used alone or in combination of two or more.
前記スチレン系単量体と共重合可能な他のビニル単量体としては、アクリロニトリル、メタクリロニトリル等のシアン化ビニル化合物、フェニルアクリレート、ベンジルアクリレート等のアクリル酸アリールエステル、メチルアクリレート、エチルアクリレート、プロピルアクリレート、ブチルアクリレート、アミルアクリレート、ヘキシルアクリレート、2−エチルヘキシルアクリレート、オクチルアクリレート、シクロヘキシルアクリレート、ドデシルアクリレート等のアクリル酸アルキルエステル、フェニルメタクリレート、ベンジルメタクリレート等のメタクリル酸アリールエステル、メチルメタクリレート、エチルメタクリレート、プロピルメタクリレート、ブチルメタクリレート、アミルメタクリレート、ヘキシルメタクリレート、2−エチルヘキシルメタクリレート、オクチルメタクリレート、シクロヘキシルメタクリレート、ドデシルメタクリレート等のメタクリル酸アルキルエステル、グリシジルメタクリレート等のエポキシ基含有メタクリル酸エステル、マレイミド、N−メチルマレイミド、N−フェニルマレイミド等のマレイミド系単量体、アクリル酸、メタクリル酸、マレイン酸、無水マレイン酸、フタル酸、イタコン酸等のα,β−不飽和カルボン酸およびその無水物が挙げられる。 Other vinyl monomers copolymerizable with the styrenic monomer include vinyl cyanide compounds such as acrylonitrile and methacrylonitrile, acrylic acid aryl esters such as phenyl acrylate and benzyl acrylate, methyl acrylate, ethyl acrylate, Acrylic acid alkyl esters such as propyl acrylate, butyl acrylate, amyl acrylate, hexyl acrylate, 2-ethylhexyl acrylate, octyl acrylate, cyclohexyl acrylate and dodecyl acrylate, aryl methacrylates such as phenyl methacrylate and benzyl methacrylate, methyl methacrylate, ethyl methacrylate, Propyl methacrylate, butyl methacrylate, amyl methacrylate, hexyl methacrylate , Methacrylate monomers such as 2-ethylhexyl methacrylate, octyl methacrylate, cyclohexyl methacrylate, dodecyl methacrylate and the like, and epoxy group-containing methacrylate esters such as glycidyl methacrylate, maleimide monomers such as maleimide, N-methylmaleimide and N-phenylmaleimide , Α, β-unsaturated carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, maleic anhydride, phthalic acid and itaconic acid, and anhydrides thereof.
前記スチレン系単量体と共重合可能なゴム成分としては、ポリブタジエン、ポリイソプレン、スチレン・ブタジエンのランダム共重合体およびブロック共重合体、アクリロニトリル・ブタジエン共重合体、アクリル酸アルキルエステルまたは/およびメタクリル酸アルキルエステルとブタジエンの共重合体、ブタジエン・イソプレン共重合体等のジエン系共重合体、エチレン・プロピレンランダム共重合体およびブロック共重合体、エチレン・ブテンのランダム共重合体およびブロック共重合体等のエチレンとα−オレフィンとの共重合体、エチレン・メタ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等のエチレンと不飽和カルボン酸エステルとの共重合体、エチレン・酢酸ビニル共重合体等のエチレンと脂肪族ビニルとの共重合体、エチレン・プロピレン・ヘキサジエン共重合体等のエチレンとプロピレンと非共役ジエンターポリマー、ポリアクリル酸ブチル等のアクリル系ゴム、およびポリオルガノシロキサンゴム成分とポリアルキル(メタ)アクリレートゴム成分とが分離できないように相互に絡み合った構造を有している複合ゴム(以下IPN型ゴム)等が挙げられる。 Examples of the rubber component copolymerizable with the styrenic monomer include polybutadiene, polyisoprene, styrene / butadiene random copolymer and block copolymer, acrylonitrile / butadiene copolymer, alkyl acrylate ester and / or methacrylic ester. Copolymers of acid alkyl esters and butadiene, diene copolymers such as butadiene / isoprene copolymers, ethylene / propylene random copolymers and block copolymers, ethylene / butene random copolymers and block copolymers Copolymers of ethylene and α-olefin, etc., ethylene / methacrylate copolymers, copolymers of ethylene and unsaturated carboxylic esters such as ethylene / butyl acrylate copolymers, ethylene / vinyl acetate copolymers, etc. Of ethylene and aliphatic vinyl Polymer, ethylene / propylene / hexadiene copolymer, etc., ethylene / propylene / non-conjugated diene terpolymer, acrylic rubber such as polybutyl acrylate, and polyorganosiloxane rubber component and polyalkyl (meth) acrylate rubber component Examples thereof include composite rubber (hereinafter referred to as IPN type rubber) having a structure in which they are intertwined so that they cannot be separated.
かかるスチレン単位成分含有樹脂(F−α−1成分)としては、例えばポリスチレン、スチレン・ブタジエン・スチレン共重合体(SBS樹脂)、水添スチレン・ブタジエン・スチレン共重合体(水添SBS樹脂)、水添スチレン・イソプレン・スチレン共重合体(水添SIS樹脂)、高衝撃ポリスチレン(HIPS樹脂)、アクリロニトリル・スチレン共重合体(AS樹脂)、アクリロニトリル・ブタジエン・スチレン共重合体(ABS樹脂)、メチルメタクリレート・ブタジエン・スチレン共重合体(MBS樹脂)、メチルメタクリレート・アクリロニトリル・ブタジエン・スチレン共重合体(MABS樹脂)、アクリロニトリル・スチレン・アクリルゴム共重合体(ASA樹脂)、アクリロニトリル・エチレンプロピレン系ゴム・スチレン共重合体(AES樹脂)、スチレン・メチルメタクリレート共重合体(MS樹脂)、メチルメタクリレート・アクリロニトリル・スチレン共重合体(MAS樹脂)、スチレン・無水マレイン酸共重合体(SMA樹脂)およびスチレン・IPN型ゴム共重合体等の樹脂、またはこれらの混合物が挙げられる。なおかかるスチレン系熱可塑性樹脂はその製造時にメタロセン触媒等の触媒使用により、シンジオタクチックポリスチレン等の高い立体規則性を有するものであってもよい。さらに場合によっては、アニオンリビング重合、ラジカルリビング重合等の方法により得られる、分子量分布の狭い重合体および共重合体、ブロック共重合体、および立体規則性の高い重合体、共重合体を使用することも可能である。これらは1種または2種以上を混合して使用することも可能である。 Examples of the styrene unit component-containing resin (F-α-1 component) include polystyrene, styrene / butadiene / styrene copolymer (SBS resin), hydrogenated styrene / butadiene / styrene copolymer (hydrogenated SBS resin), Hydrogenated styrene / isoprene / styrene copolymer (hydrogenated SIS resin), high impact polystyrene (HIPS resin), acrylonitrile / styrene copolymer (AS resin), acrylonitrile / butadiene / styrene copolymer (ABS resin), methyl Methacrylate / butadiene / styrene copolymer (MBS resin), methyl methacrylate / acrylonitrile / butadiene / styrene copolymer (MABS resin), acrylonitrile / styrene / acrylic rubber copolymer (ASA resin), acrylonitrile / ethylene propylene rubber / Sti Copolymer (AES resin), styrene / methyl methacrylate copolymer (MS resin), methyl methacrylate / acrylonitrile / styrene copolymer (MAS resin), styrene / maleic anhydride copolymer (SMA resin) and styrene / Examples thereof include resins such as an IPN type rubber copolymer, or a mixture thereof. Such a styrenic thermoplastic resin may have a high stereoregularity such as syndiotactic polystyrene by using a catalyst such as a metallocene catalyst during the production thereof. Further, in some cases, polymers and copolymers having a narrow molecular weight distribution, block copolymers, polymers with high stereoregularity, and copolymers obtained by anionic living polymerization, radical living polymerization, or the like are used. It is also possible. These may be used alone or in combination of two or more.
これらの中でもポリスチレン(PS樹脂)、高衝撃ポリスチレン(HIPS樹脂)、アクリロニトリル・スチレン共重合体(AS樹脂)、アクリロニトリル・ブタジエン・スチレン共重合体(ABS樹脂)、アクリロニトリル・スチレン・アクリルゴム共重合体(ASA樹脂)、アクリロニトリル・エチレンプロピレン系ゴム・スチレン共重合体(AES樹脂)メチルメタクリレート・ブタジエン・スチレン共重合体(MBS樹脂)からなる群より選択される1種または2種以上を混合して使用することが好ましく、中でもABS樹脂、ASA樹脂、AES樹脂が最も好ましい。 Among these, polystyrene (PS resin), high impact polystyrene (HIPS resin), acrylonitrile / styrene copolymer (AS resin), acrylonitrile / butadiene / styrene copolymer (ABS resin), acrylonitrile / styrene / acrylic rubber copolymer (ASA resin), acrylonitrile / ethylene propylene rubber / styrene copolymer (AES resin), one or more selected from the group consisting of methyl methacrylate / butadiene / styrene copolymer (MBS resin) Preferably, ABS resin, ASA resin, and AES resin are most preferable.
本発明で使用するABS樹脂とは、ジエン系ゴム成分にシアン化ビニル化合物と芳香族ビニル化合物をグラフト重合した熱可塑性グラフト共重合体(ABS共重合体)とシアン化ビニル化合物と芳香族ビニル化合物の共重合体(AS共重合体)の混合物である。なお、このシアン化ビニル化合物と芳香族ビニル化合物との共重合体はジエン系ゴム成分にシアン化ビニル化合物と芳香族ビニル化合物とをグラフト共重合した熱可塑性グラフト共重合体からなる樹脂の製造の際に副生される共重合体でもよく、芳香族ビニル化合物とシアン化ビニル化合物とを別途共重合して得られる共重合体でもよい。かかるシアン化ビニル化合物および芳香族ビニル化合物からなる共重合体の分子量は、好ましくは還元粘度で0.2〜1.0、より好ましくは0.25〜0.5であるものである。尚、かかるAS共重合体の割合は、アセトンなどのかかるAS共重合体の良溶媒にABS樹脂を溶解し、その可溶分を遠心分離するなどの手法により採取することが可能である。一方その不溶分(ゲル)が正味のABS共重合体となる。 The ABS resin used in the present invention is a thermoplastic graft copolymer (ABS copolymer) obtained by graft polymerization of a vinyl cyanide compound and an aromatic vinyl compound to a diene rubber component, a vinyl cyanide compound and an aromatic vinyl compound. It is a mixture of the copolymer (AS copolymer). The copolymer of the vinyl cyanide compound and the aromatic vinyl compound is used for the production of a resin comprising a thermoplastic graft copolymer obtained by graft copolymerizing a vinyl cyanide compound and an aromatic vinyl compound with a diene rubber component. It may be a copolymer produced as a by-product, or a copolymer obtained by separately copolymerizing an aromatic vinyl compound and a vinyl cyanide compound. The molecular weight of the copolymer comprising the vinyl cyanide compound and the aromatic vinyl compound is preferably 0.2 to 1.0, more preferably 0.25 to 0.5 in terms of reduced viscosity. The ratio of the AS copolymer can be collected by a technique such as dissolving the ABS resin in a good solvent for the AS copolymer such as acetone and centrifuging the soluble component. On the other hand, the insoluble matter (gel) becomes a net ABS copolymer.
またグラフトされたシアン化ビニル化合物および芳香族ビニル化合物のジエン系ゴム成分に対する重量割合(グラフト率)は20〜200重量%が好ましく、より好ましくは20〜70重量%のグラフト率のものである。 Further, the weight ratio (graft ratio) of the grafted vinyl cyanide compound and aromatic vinyl compound to the diene rubber component is preferably 20 to 200% by weight, more preferably 20 to 70% by weight.
ABS樹脂を形成するジエン系ゴム成分としては、例えばポリブタジエン、ポリイソプレンおよびスチレン−ブタジエン共重合体等のガラス転移点が10℃以下のゴムが用いられ、その割合はABS樹脂成分100重量%中5〜39.9重量%であるのが好ましく、より好ましくは10〜35重量%、さらに好ましくは10〜25重量%である。 As the diene rubber component forming the ABS resin, for example, a rubber having a glass transition point of 10 ° C. or lower such as polybutadiene, polyisoprene, and styrene-butadiene copolymer is used, and the ratio is 5% in 100% by weight of the ABS resin component. It is preferable that it is -39.9 weight%, More preferably, it is 10-35 weight%, More preferably, it is 10-25 weight%.
ジエン系ゴム成分にグラフトされるシアン化ビニル化合物としては、前記のものを挙げることができ、特にアクリロニトリルが好ましく使用できる。またジエン系ゴム成分にグラフトされる芳香族ビニル化合物としては、同様に前記のものを使用できるが、特にスチレンおよびα−メチルスチレンが好ましく使用できる。かかるジエン系ゴム成分にグラフトされる成分の割合は、ABS樹脂成分100重量%中60.1〜95重量%が好ましく、より好ましくは65〜90重量%、さらに好ましくは75〜90重量%である。さらにかかるシアン化ビニル化合物および芳香族ビニル化合物の合計量100重量%に対して、シアン化ビニル化合物が5〜50重量%およびより好ましくは10〜30重量%、並びに芳香族ビニル化合物が95〜50重量%およびより好ましくは90〜70重量%であることが好ましい。さらに上記のジエン系ゴム成分にグラフトされる成分の一部についてメチル(メタ)アクリレート、エチルアクリレート、無水マレイン酸、N置換マレイミド等を混合使用することもでき、これらの含有割合はABS樹脂成分中15重量%以下であるものが好ましい。さらに反応で使用する開始剤、連鎖移動剤、乳化剤等は必要に応じて、従来公知の各種のものが使用可能である。 Examples of the vinyl cyanide compound grafted onto the diene rubber component include those described above, and acrylonitrile is particularly preferably used. As the aromatic vinyl compound grafted onto the diene rubber component, those described above can be used in the same manner, but styrene and α-methylstyrene are particularly preferably used. The proportion of the component grafted to the diene rubber component is preferably 60.1 to 95% by weight, more preferably 65 to 90% by weight, and further preferably 75 to 90% by weight in 100% by weight of the ABS resin component. . Further, the vinyl cyanide compound is 5 to 50% by weight and more preferably 10 to 30% by weight and the aromatic vinyl compound is 95 to 50% with respect to 100% by weight of the total amount of the vinyl cyanide compound and the aromatic vinyl compound. It is preferred to be 90% by weight and more preferably 90-70% by weight. Further, methyl (meth) acrylate, ethyl acrylate, maleic anhydride, N-substituted maleimide and the like can be mixed and used for some of the components grafted to the diene rubber component, and the content ratio thereof is in the ABS resin component. What is 15 weight% or less is preferable. Furthermore, conventionally well-known various things can be used for the initiator, chain transfer agent, emulsifier, etc. which are used by reaction as needed.
ABS樹脂においては、ゴム粒子径は0.1〜5.0μmが好ましく、より好ましくは0.3〜3.0μm、さらに好ましくは0.4〜1.5μm、特に好ましくは0.4〜0.9μmである。かかるゴム粒子径の分布は単一の分布であるものおよび2山以上の複数の山を有するもののいずれもが使用可能であり、さらにそのモルフォロジーにおいてもゴム粒子が単一の相をなすものであっても、ゴム粒子の周りにオクルード相を含有することによりサラミ構造を有するものであってもよい。 In the ABS resin, the rubber particle diameter is preferably from 0.1 to 5.0 μm, more preferably from 0.3 to 3.0 μm, still more preferably from 0.4 to 1.5 μm, particularly preferably from 0.4 to 0.00. 9 μm. As the distribution of the rubber particle diameter, both a single distribution and a rubber particle having a plurality of peaks can be used, and the rubber particles form a single phase in the morphology. Alternatively, it may have a salami structure by containing an occluded phase around the rubber particles.
このABS樹脂は塊状重合、懸濁重合、乳化重合のいずれの方法で製造されたものでもよく、また共重合の方法も一段で共重合しても、多段で共重合してもよい。さらに重合法としては一般的な乳化重合法の他、過硫酸カリウム等の開始剤を使用するソープフリー重合法、シード重合法、二段階膨潤重合法等を挙げることができる。また懸濁重合法において、水相とモノマー相とを個別に保持して両者を正確に連続式の分散機に供給し、粒子径を分散機の回転数で制御する方法や、連続式の製造方法において分散能を有する水性液体中にモノマー相を数〜数十μm径の細径オリフィスまたは多孔質フィルターを通すことにより供給し粒径を制御する方法などを行ってもよい。 This ABS resin may be produced by any of bulk polymerization, suspension polymerization, and emulsion polymerization, and the copolymerization method may be one-stage copolymerization or multistage copolymerization. Furthermore, examples of the polymerization method include a general emulsion polymerization method, a soap-free polymerization method using an initiator such as potassium persulfate, a seed polymerization method, and a two-stage swelling polymerization method. In the suspension polymerization method, the water phase and the monomer phase are maintained separately, and both are accurately supplied to the continuous disperser, and the particle diameter is controlled by the rotation speed of the disperser, and the continuous production is performed. In the method, a method may be used in which the monomer phase is supplied by passing it through a fine orifice having a diameter of several to several tens of μm or a porous filter in an aqueous liquid having dispersibility to control the particle size.
本発明で使用するASA樹脂とは、アクリルゴム成分にシアン化ビニル化合物と芳香族ビニル化合物をグラフト重合した熱可塑性グラフト共重合体、または該熱可塑性グラフト共重合体と、シアン化ビニル化合物と芳香族ビニル化合物の共重合体との混合物をいう。本発明でいうアクリルゴムとは、炭素数が2〜10のアルキルアクリレート単位を含有するものであり、さらに必要に応じてその他の共重合可能な成分として、スチレン、メチルメタクリレート、ブタジエンを含有してもよい。炭素数が2〜10のアルキルアクリレートとして好ましくは2−エチルヘキシルアクリレート、n−ブチルアクリレートが挙げられ、かかるアルキルアクリレートはアクリレートゴム100重量%中50重量%以上含まれるものが好ましい。さらにかかるアクリレートゴムは少なくとも部分的に架橋されており、かかる架橋剤としては、エチレングリコールジアクリレート、ブチレングリコールジアクリレート、エチレングリコールジメタクリレート、アリルメタクリレート、ポリプロピレングリコールジアクリレート等を挙げることができ、かかる架橋剤はアクリレートゴムに対して0.01〜3重量%使用されることが好ましい。アクリルゴム成分の割合は、ASA樹脂100重量%中、5〜39.9重量%が好ましく、より好ましくは10〜35重量%、さらに好ましくは10〜25重量%である。 The ASA resin used in the present invention is a thermoplastic graft copolymer obtained by graft polymerization of a vinyl cyanide compound and an aromatic vinyl compound to an acrylic rubber component, or the thermoplastic graft copolymer, a vinyl cyanide compound and an aromatic resin. A mixture with a copolymer of a group vinyl compound. The acrylic rubber referred to in the present invention contains an alkyl acrylate unit having 2 to 10 carbon atoms, and further contains styrene, methyl methacrylate, butadiene as other copolymerizable components as necessary. Also good. Preferred examples of the alkyl acrylate having 2 to 10 carbon atoms include 2-ethylhexyl acrylate and n-butyl acrylate. The alkyl acrylate is preferably contained in an amount of 50% by weight or more in 100% by weight of the acrylate rubber. Further, the acrylate rubber is at least partially crosslinked, and examples of the crosslinking agent include ethylene glycol diacrylate, butylene glycol diacrylate, ethylene glycol dimethacrylate, allyl methacrylate, polypropylene glycol diacrylate, and the like. The crosslinking agent is preferably used in an amount of 0.01 to 3% by weight based on the acrylate rubber. The proportion of the acrylic rubber component is preferably 5 to 39.9% by weight, more preferably 10 to 35% by weight, and still more preferably 10 to 25% by weight in 100% by weight of the ASA resin.
またシアン化ビニル化合物および芳香族ビニル化合物の割合はかかる合計量100重量%に対して、シアン化ビニル化合物が5〜50重量%、芳香族ビニル化合物が95〜50重量%であり、特にシアン化ビニル化合物が15〜35重量%、芳香族ビニル化合物が85〜65重量%のものが好ましい。製造法としては上記ABS樹脂と同様のものを使用することが可能である。 The proportion of the vinyl cyanide compound and the aromatic vinyl compound is 5 to 50% by weight of the vinyl cyanide compound and 95 to 50% by weight of the aromatic vinyl compound with respect to the total amount of 100% by weight. It is preferable that the vinyl compound is 15 to 35% by weight and the aromatic vinyl compound is 85 to 65% by weight. As the production method, the same one as the above ABS resin can be used.
本発明で使用するAES樹脂とは、エチレン−プロピレンゴム成分またはエチレン−プロピレン−ジエンゴム成分にシアン化ビニル化合物と芳香族ビニル化合物をグラフト重合した熱可塑性グラフト共重合体、又は該熱可塑性グラフト共重合体と、シアン化ビニル化合物と芳香族ビニル化合物の共重合体との混合物である。製造法としては上記ABS樹脂と同様のものを使用することが可能である。 The AES resin used in the present invention is a thermoplastic graft copolymer obtained by graft polymerization of a vinyl cyanide compound and an aromatic vinyl compound to an ethylene-propylene rubber component or an ethylene-propylene-diene rubber component, or the thermoplastic graft copolymer. And a mixture of a vinyl cyanide compound and a copolymer of an aromatic vinyl compound. As the production method, the same one as the above ABS resin can be used.
(F−α−2成分)
ゴム成分含有量40重量%以上のスチレン単位含有樹脂としては、ガラス転移温度が10℃以下のゴム成分に、芳香族ビニル、シアン化ビニル、アクリル酸エステル、メタクリル酸エステル、およびこれらと共重合可能なビニル単量体の1種または2種以上が共重合されたグラフト共重合体を挙げることができる。
(F-α-2 component)
As a styrene unit-containing resin having a rubber component content of 40% by weight or more, a rubber component having a glass transition temperature of 10 ° C. or less can be copolymerized with aromatic vinyl, vinyl cyanide, acrylate ester, methacrylate ester, and the like. Examples thereof include graft copolymers obtained by copolymerizing one or more vinyl monomers.
またかかるゴム成分と上記モノマーのブロック共重合体も挙げられる。かかるブロック共重合体としては具体的にはスチレン・エチレンプロピレン・スチレンエラストマー(水添スチレン・イソプレン・スチレンエラストマー)、および水添スチレン・ブタジエン・スチレンエラストマーなどの熱可塑性エラストマーを挙げることができる。 Moreover, the rubber component and the block copolymer of the said monomer are also mentioned. Specific examples of such block copolymers include thermoplastic elastomers such as styrene / ethylenepropylene / styrene elastomers (hydrogenated styrene / isoprene / styrene elastomers) and hydrogenated styrene / butadiene / styrene elastomers.
さらに他の熱可塑性エラストマーして知られている各種の弾性重合体、例えばポリウレタンエラストマー、ポリエステルエラストマー、ポリエーテルアミドエラストマー等を使用することも可能である。 Furthermore, various elastic polymers known as other thermoplastic elastomers such as polyurethane elastomers, polyester elastomers, polyether amide elastomers and the like can also be used.
なお、かかるゴム成分含有量40重量%以上のスチレン単位成分含有樹脂は、ゴム成分を40%以上含有するものであり、この点で本発明の40重量%未満のスチレン単位成分含有樹脂とは明確に区別されるものである。 The styrene unit component-containing resin having a rubber component content of 40% by weight or more contains a rubber component of 40% or more. In this respect, the styrene unit component-containing resin having a rubber component content of less than 40% by weight is clear. Are distinguished.
ここでいうガラス転移温度が10℃以下のゴム成分としては、ブタジエンゴム、ブタジエン−アクリル複合ゴム、アクリルゴム、アクリル−シリコン複合ゴム、イソブチレン−シリコン複合ゴム、イソプレンゴム、スチレン−ブタジエンゴム、クロロプレンゴム、エチレン−プロピレンゴム、ニトリルゴム、エチレン−アクリルゴム、シリコンゴム、エピクロロヒドリンゴム、フッ素ゴムおよびこれらの不飽和結合部分に水素が添加されたものを挙げることができる。 As the rubber component having a glass transition temperature of 10 ° C. or less here, butadiene rubber, butadiene-acrylic composite rubber, acrylic rubber, acrylic-silicon composite rubber, isobutylene-silicon composite rubber, isoprene rubber, styrene-butadiene rubber, chloroprene rubber , Ethylene-propylene rubber, nitrile rubber, ethylene-acrylic rubber, silicon rubber, epichlorohydrin rubber, fluororubber, and those obtained by adding hydrogen to these unsaturated bonds.
中でもガラス転移温度が−10℃以下、より好ましくは−30℃以下のゴム成分を含有する衝撃改質材が好ましく、特にブタジエンゴム、ブタジエン−アクリル複合ゴム、アクリルゴム、アクリル−シリコン複合ゴムを使用した衝撃改質材が好ましい。複合ゴムとは、2種のゴム成分を共重合したゴムまたは分離できないよう相互に絡み合ったIPN構造をとるように重合したゴムをいう。 Among them, impact modifiers containing a rubber component having a glass transition temperature of −10 ° C. or lower, more preferably −30 ° C. or lower are preferable. Particularly, butadiene rubber, butadiene-acrylic composite rubber, acrylic rubber, and acrylic-silicon composite rubber are used. Preferred impact modifiers are preferred. The composite rubber is a rubber obtained by copolymerizing two kinds of rubber components or a rubber polymerized so as to have an IPN structure entangled with each other so as not to be separated.
芳香族ビニルとしては、スチレン、α−メチルスチレン、p−メチルスチレン、アルコキシスチレン、ハロゲン化スチレン等を挙げることができ、特にスチレンが好ましい。またアクリル酸エステルとしては、アクリル酸メチル、アクリル酸エチル、アクリル酸ブチル、アクリル酸シクロヘキシル、アクリル酸オクチル等を挙げることができ、メタアクリル酸エステルとしては、メタクリル酸メチル、メタクリル酸エチル、メタクリル酸ブチル、メタクリル酸シクロヘキシル、メタクリル酸オクチル等を挙げることができ、メタクリル酸メチルが特に好ましい。 Examples of the aromatic vinyl include styrene, α-methylstyrene, p-methylstyrene, alkoxystyrene, halogenated styrene and the like, and styrene is particularly preferable. Examples of acrylic esters include methyl acrylate, ethyl acrylate, butyl acrylate, cyclohexyl acrylate, octyl acrylate, etc., and examples of methacrylic esters include methyl methacrylate, ethyl methacrylate, methacrylic acid. Examples thereof include butyl, cyclohexyl methacrylate, octyl methacrylate and the like, and methyl methacrylate is particularly preferable.
ガラス転移温度が10℃以下のゴム成分を含有する衝撃改質材は、塊状重合、溶液重合、懸濁重合、乳化重合のいずれの重合法で製造したものであってもよく、共重合の方式は一段グラフトであっても多段グラフトであっても差し支えない。また製造の際に副生するグラフト成分のみのコポリマーとの混合物であってもよい。さらに重合法としては一般的な乳化重合法の他、過硫酸カリウム等の開始剤を使用するソープフリー重合法、シード重合法、二段階膨潤重合法等を挙げることができる。また懸濁重合法において、水相とモノマー相とを個別に保持して両者を正確に連続式の分散機に供給し、粒子径を分散機の回転数で制御する方法、および連続式の製造方法において分散能を有する水性液体中にモノマー相を数〜数十μm径の細径オリフィスまたは多孔質フィルターを通すことにより供給し粒径を制御する方法などを行ってもよい。 The impact modifier containing a rubber component having a glass transition temperature of 10 ° C. or lower may be produced by any polymerization method of bulk polymerization, solution polymerization, suspension polymerization, and emulsion polymerization, and is a copolymerization method. May be a single-stage graft or a multi-stage graft. Moreover, the mixture with the copolymer of only the graft component byproduced in the case of manufacture may be sufficient. Furthermore, examples of the polymerization method include a general emulsion polymerization method, a soap-free polymerization method using an initiator such as potassium persulfate, a seed polymerization method, and a two-stage swelling polymerization method. In the suspension polymerization method, the aqueous phase and the monomer phase are individually maintained, both are accurately supplied to the continuous disperser, and the particle diameter is controlled by the rotation speed of the disperser, and the continuous production is performed. In the method, a method may be used in which the monomer phase is supplied by passing it through a fine orifice having a diameter of several to several tens of μm or a porous filter in an aqueous liquid having dispersibility to control the particle size.
かかる衝撃改質材は市販されており容易に入手することが可能である。例えばガラス転移温度が10℃以下のゴム成分として、ブタジエンゴム、アクリルゴムまたはブタジエン−アクリル複合ゴムを主体とするものとしては、鐘淵化学工業(株)のカネエースBシリーズ、三菱レイヨン(株)のメタブレンCシリーズ、呉羽化学工業(株)のEXLシリーズ、HIAシリーズ、BTAシリーズ、KCAシリーズ、宇部サイコン(株)のUCLモディファイヤーレジンシリーズが挙げられ、ガラス転移温度が10℃以下のゴム成分としてアクリル−シリコン複合ゴムを主体とするものとしては三菱レイヨン(株)よりメタブレンS−2001あるいはSRK−200という商品名で市販されているものが挙げられる。 Such impact modifiers are commercially available and can be easily obtained. For example, as a rubber component having a glass transition temperature of 10 ° C. or less, butadiene rubber, acrylic rubber or butadiene-acrylic composite rubber is mainly used as Kane Ace B series of Kaneka Chemical Industry Co., Ltd., Mitsubishi Rayon Co., Ltd. Examples include METABLEN C series, Kureha Chemical Industry's EXL series, HIA series, BTA series, KCA series, Ube modifier resin series UCL modifier resin series, and acrylic as a rubber component with a glass transition temperature of 10 ° C or less. -As what mainly has a silicon composite rubber, what is marketed by Mitsubishi Rayon Co., Ltd. by the brand name of Metablen S-2001 or SRK-200 is mentioned.
かかるゴム成分含有量40重量%未満のスチレン単位成分含有樹脂と、スチレン単位成分含有樹脂とゴム成分含有量40重量%以上のスチレン単位成分含有樹脂との併用は、耐衝撃性を更に高め、その好ましい態様として、ゴム成分含有量40重量%未満のスチレン単位成分含有樹脂100重量に対し、ゴム成分含有量40重量%以上のスチレン単位成分含有樹脂を0.5〜50重量部含有する態様が挙げられる。 The combined use of the styrene unit component-containing resin having a rubber component content of less than 40% by weight, and the styrene unit component-containing resin and the styrene unit component-containing resin having a rubber component content of 40% by weight or more further increases impact resistance. A preferred embodiment is an embodiment in which 0.5 to 50 parts by weight of a styrene unit component-containing resin having a rubber component content of 40% by weight or more is contained per 100 parts by weight of a styrene unit component-containing resin having a rubber component content of less than 40% by weight. It is done.
(F−β成分)
本発明の実質的にゴム成分を含まない衝撃改質剤(F−β成分)として、共重合ポリエステル、共重合ポリエチレンからなる群より選ばれる少なくとも一種の樹脂が好ましい。
共重合ポリエステルとしては、ポリ乳酸成分を含む共重合ポリエステル、ポリブチレンアジペートテレフタレート成分を含む星型構造を有する共重合ポリエステルなどが例示される。具体的には例えば大日本インキ化学工業(株)よりプラメートの商品名で販売されているプラメート PD−150、PD−350などが例示される。またBASFジャパン(株)よりエコフレックス(Ecoflex)の商品名で販売されているEcoflex SBX7025が例示される。
(F-β component)
As the impact modifier (F-β component) containing substantially no rubber component of the present invention, at least one resin selected from the group consisting of copolymerized polyester and copolymerized polyethylene is preferable.
Examples of the copolyester include a copolyester containing a polylactic acid component and a copolyester having a star structure containing a polybutylene adipate terephthalate component. Specifically, for example, Plumate PD-150 and PD-350 sold under the trade name of Puramate from Dainippon Ink and Chemicals, Inc. are exemplified. Moreover, Ecoflex SBX7025 sold by BASF Japan Co., Ltd. under the trade name of Ecoflex is exemplified.
共重合ポリエチレンとしては例えば住友化学(株)よりボンドファストの商品名で市販されているエチレン、グリシジルメタクリレートよりなるボンドファストE、さらにアクリル酸メチルユニットを含む同7M、DuPont社製Biomax Strong100などが例示される。 Examples of the copolymer polyethylene include ethylene marketed by Sumitomo Chemical Co., Ltd. under the trade name Bondfast, Bondfast E made of glycidyl methacrylate, 7M containing methyl acrylate units, and BioMax Strong100 manufactured by DuPont. Is done.
ポリエステルエラストマーは、ポリブチレンテレフタレート骨格を主たる骨格とし、ポリアルキレングリコールが共重合されたエラストマーであり、例えば帝人(株)製TR−EL−1などが例示される。 The polyester elastomer is an elastomer in which a polybutylene terephthalate skeleton is a main skeleton and a polyalkylene glycol is copolymerized. Examples thereof include TR-EL-1 manufactured by Teijin Limited.
ポリアミドエラストマーは、ポリアミドオリゴマーをハードセグメントとし、ポリエステルまたはポリエーテルエステルをソフトセグメントとするエラストマーであり、例えば富士化成工業(株)社製TPAE31、TPAE32、TPAE38などが例示される。 The polyamide elastomer is an elastomer having a polyamide oligomer as a hard segment and a polyester or polyether ester as a soft segment, and examples thereof include TPAE31, TPAE32, and TPAE38 manufactured by Fuji Kasei Kogyo Co., Ltd.
衝撃改質剤(F成分)の含有量は、樹脂成分(A成分)100重量部に対して、2〜100重量部、より好ましくは3〜90重量部、さらに好ましくは5〜80重量部である。含有量が2重量部未満では衝撃改質剤の添加量が少なすぎ、十分な耐加水分解性が得られず、100重量部を超えると耐熱性が悪化して離型性が低下し、寸法安定性が悪化するため、好ましくない。 The content of the impact modifier (F component) is 2 to 100 parts by weight, more preferably 3 to 90 parts by weight, and even more preferably 5 to 80 parts by weight with respect to 100 parts by weight of the resin component (component A). is there. If the content is less than 2 parts by weight, the amount of impact modifier added is too small, and sufficient hydrolysis resistance cannot be obtained. If the content exceeds 100 parts by weight, the heat resistance is deteriorated and the releasability is reduced. Since stability deteriorates, it is not preferable.
〈難燃剤:G成分〉
本発明の組成物は難燃剤(G成分)を含有してもよい。難燃剤(G成分)としては、リン系難燃剤(G−1成分)、窒素系難燃剤(G−2成分)、水酸化金属化合物系難燃剤(G−3成分)が挙げられる。これら3種の使用は単独でも2種以上でも良く、各々の種類の中で単数以上の化合物を使用しても構わない。その使用は目的に応じて使い分けることが好ましい。
<Flame retardant: G component>
The composition of the present invention may contain a flame retardant (G component). Examples of the flame retardant (G component) include phosphorus-based flame retardant (G-1 component), nitrogen-based flame retardant (G-2 component), and metal hydroxide compound-based flame retardant (G-3 component). These three types may be used alone or in combination of two or more, and a single or more compounds may be used in each type. It is preferable to use it properly according to the purpose.
(リン系難燃剤:G−1成分)
リン系難燃剤(G−1成分)としては、(1)リン酸エステル系難燃剤、(2)ホスホニトリル系難燃剤、(3)ホスホネート系難燃剤、(4)ポリリン酸塩系難燃剤、(5)ホスフィン酸塩系が挙げられる。
(Phosphorus flame retardant: G-1 component)
As phosphorus flame retardant (G-1 component), (1) phosphate ester flame retardant, (2) phosphonitrile flame retardant, (3) phosphonate flame retardant, (4) polyphosphate flame retardant, (5) A phosphinic acid salt type is mentioned.
(1)リン酸エステル系難燃剤
リン酸エステル系難燃剤の具体例としては、特に下記式(5)で表される1種または2種以上のリン酸エステル化合物を挙げることができる。
(1) Phosphate ester flame retardant Specific examples of the phosphate ester flame retardant include one or more phosphate ester compounds represented by the following formula (5).
式中Xは、ハイドロキノン、レゾルシノール、ビス(4−ヒドロキシジフェニル)メタン、ビスフェノールA、ジヒドロキシジフェニル、ジヒドロキシナフタレン、ビス(4−ヒドロキシフェニル)スルホン、ビス(4−ヒドロキシフェニル)ケトン、ビス(4−ヒドロキシフェニル)サルファイドから誘導される基である。nは0〜5の整数であり、またはn数の異なるリン酸エステルの混合物の場合は0〜5の平均値である。R11、R12、R13、およびR14はそれぞれ独立して1個以上のハロゲン原子を置換したもしくは置換していないフェノール、クレゾール、キシレノール、イソプロピルフェノール、ブチルフェノール、p−クミルフェノールから誘導される基である。 In the formula, X is hydroquinone, resorcinol, bis (4-hydroxydiphenyl) methane, bisphenol A, dihydroxydiphenyl, dihydroxynaphthalene, bis (4-hydroxyphenyl) sulfone, bis (4-hydroxyphenyl) ketone, bis (4-hydroxy It is a group derived from phenyl) sulfide. n is an integer of 0 to 5, or an average value of 0 to 5 in the case of a mixture of phosphate esters having different n numbers. R 11 , R 12 , R 13 , and R 14 are each independently derived from phenol, cresol, xylenol, isopropylphenol, butylphenol, p-cumylphenol substituted or unsubstituted with one or more halogen atoms. It is a group.
さらに好ましいものとしては、式中のXが、ハイドロキノン、レゾルシノール、ビスフェノールA、およびジヒドロキシジフェニルから誘導される基であり、nは1〜3の整数であり、またはn数の異なるリン酸エステルのブレンドの場合はその平均値であり、R11、R12、R13、およびR14はそれぞれ独立して1個以上のハロゲン原子を置換したもしくはより好適には置換していないフェノール、クレゾール、キシレノールから誘導される基であるものが挙げられる。 More preferably, X in the formula is a group derived from hydroquinone, resorcinol, bisphenol A, and dihydroxydiphenyl, n is an integer of 1 to 3, or a blend of n different phosphate esters. In the case of R 11 , R 12 , R 13 , and R 14 each independently from phenol, cresol, or xylenol that is substituted or more preferably substituted with one or more halogen atoms. Those that are groups to be derived are mentioned.
かかる有機リン酸エステル系難燃剤の中でも、ホスフェート化合物としてはトリフェニルホスフェート、ホスフェートオリゴマーとしてはレゾルシノールビス(ジキシレニルホスフェート)およびビスフェノールAビス(ジフェニルホスフェート)が耐加水分解性などにも優れるため好ましく使用できる。さらに好ましいのは、耐熱性などの点からレゾルシノールビス(ジキシレニルホスフェート)およびビスフェノールAビス(ジフェニルホスフェート)である。これらは耐熱性も良好であるためそれらが熱劣化したり揮発するなどの弊害がないためである。 Among such organophosphate flame retardants, triphenyl phosphate is preferable as a phosphate compound, and resorcinol bis (dixylenyl phosphate) and bisphenol A bis (diphenyl phosphate) are preferable as phosphate oligomers because of excellent hydrolysis resistance. Can be used. More preferable are resorcinol bis (dixylenyl phosphate) and bisphenol A bis (diphenyl phosphate) from the viewpoint of heat resistance. This is because they have good heat resistance and are free from adverse effects such as thermal deterioration and volatilization.
(2)ホスホニトリル系難燃剤
本発明で用いられるホスホニトリル系難燃剤は、ホスホニトリル線状ポリマーおよび/または環状ポリマーであり、下記式(6)で表される繰り返し単位を有するオリゴマーないしポリマーであり、その数平均重合度が3以上のものである。直鎖状、環状のいずれであってもかまわないが、特に環状3量体が好ましく用いられる。また、直鎖状物、環状物を任意の割合で混合した
混合物であってもかまわない。
(2) Phosphononitrile-based flame retardant The phosphonitrile-based flame retardant used in the present invention is a phosphonitrile linear polymer and / or a cyclic polymer, and is an oligomer or polymer having a repeating unit represented by the following formula (6). The number average degree of polymerization is 3 or more. Although it may be either linear or cyclic, a cyclic trimer is particularly preferably used. Further, it may be a mixture in which a linear product and a cyclic product are mixed at an arbitrary ratio.
式中A、Bは各々独立に、O、N、S原子を表わす。R1、R2は各々独立に、炭素数6〜15のアリール基、炭素数6〜15のアルキル基、炭素数6〜15のアラルキル基、または炭素数6〜15のシクロアルキル基である。R1とR2が連結した環状構造でも良い。x、yは、0または1である。nは数平均重合度を意味し、3または3より大きい数値を表わす。 In the formula, A and B each independently represent an O, N, or S atom. R 1 and R 2 are each independently an aryl group having 6 to 15 carbon atoms, an alkyl group having 6 to 15 carbon atoms, an aralkyl group having 6 to 15 carbon atoms, or a cycloalkyl group having 6 to 15 carbon atoms. R 1 and R 2 may be a cyclic structure linked. x and y are 0 or 1. n means the number average degree of polymerization and represents a value of 3 or more.
かかるホスホニトリル線状ポリマーおよび/または環状ポリマーは、ヘキサクロロシクロトリホスファゼン、オクタクロロシクロテトラホスファゼン、あるいはこれら環状オリゴマーを開環重合して得られるポリ(ジクロロホスファゼン)とアルコール、フェノール、アミン、チオール、グリニャール試薬等の求核試薬とを公知の方法で反応させることにより合成することができる。 Such phosphonitrile linear polymers and / or cyclic polymers include hexachlorocyclotriphosphazene, octachlorocyclotetraphosphazene, or poly (dichlorophosphazene) obtained by ring-opening polymerization of these cyclic oligomers and alcohol, phenol, amine, thiol, It can be synthesized by reacting with a nucleophilic reagent such as a Grignard reagent by a known method.
(3)ホスホネート系難燃剤
ホスホネート系難燃剤は、下記一般式(7)で表されるものが好ましい。
(3) Phosphonate flame retardant The phosphonate flame retardant is preferably represented by the following general formula (7).
式中R1およびR2は各々独立に、炭素数1〜24の分岐もしくは分岐していないアルキレン基、炭素数6〜20の置換もしくは非置換のアリーレン基、炭素数6〜30の置換もしくは非置換のアラルキレン(aralkylene)基、または炭素数6〜30の置換もしくは非置換のアルカリーレン(alkarylene)基である。 In the formula, each of R 1 and R 2 independently represents a branched or unbranched alkylene group having 1 to 24 carbon atoms, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms, a substituted or non-substituted group having 6 to 30 carbon atoms. A substituted aralkylene group, or a substituted or unsubstituted alkarylene group having 6 to 30 carbon atoms.
R3は、水素原子、炭素数1〜24の分岐若しくは分岐していないアルキル基、炭素数6〜20の置換もしくは非置換のアリール基、炭素数6〜30の置換もしくは非置換のアラルキル基、または炭素数6〜30の置換もしくは非置換のアルカリール(alkaryl)基である。xおよびyはそれぞれ独立して1〜50の数である。 R 3 is a hydrogen atom, a branched or unbranched alkyl group having 1 to 24 carbon atoms, a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, Or it is a C6-C30 substituted or unsubstituted alkaryl group. x and y are each independently a number from 1 to 50.
(4)ポリリン酸塩系難燃剤
本発明で用いられるポリリン酸塩系難燃剤として、ポリリン酸アンモニウム、ポリリン酸メラミン等が挙げられる。
(4) Polyphosphate flame retardant Examples of the polyphosphate flame retardant used in the present invention include ammonium polyphosphate and melamine polyphosphate.
(5)ホスフィン酸塩系難燃剤
本発明で用いられるホスフィン酸塩系難燃剤として、下記式(8)または下記式(9)で表される塩が挙げられる。
(5) Phosphinate Flame Retardant Examples of the phosphinate flame retardant used in the present invention include salts represented by the following formula (8) or the following formula (9).
式中R11、R12は各々独立に、炭素数1〜20の直鎖もしくは分岐のアルキル基、炭素数6〜20のシクロアルキル基、炭素数6〜20のアリール基、炭素数7〜20のアラルキル基である。R13は、炭素数1〜20の直鎖または分岐のアルキレン基、炭素数6〜20のシクロアルキレン基、炭素数6〜20のアリーレン基、炭素数7〜20のアルキレンアリーレン基またはシクロアルキレンアリーレン基である。Mは、Mg、Ca、Al、Sb、Sn、Ge、Ti、Zn、Fe、Zn、Ce、Bi、Sr、Mn、Li、Na、Kまたはプロトン化した窒素塩基である。xは1または2である。mは2または3であり、nは1または3である。 Each independently wherein R 11, R 12 is a straight-chain or branched alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 6 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, 7 to 20 carbon atoms Is an aralkyl group. R 13 represents a linear or branched alkylene group having 1 to 20 carbon atoms, a cycloalkylene group having 6 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, an alkylene arylene group having 7 to 20 carbon atoms or a cycloalkylene arylene group. It is a group. M is Mg, Ca, Al, Sb, Sn, Ge, Ti, Zn, Fe, Zn, Ce, Bi, Sr, Mn, Li, Na, K, or a protonated nitrogen base. x is 1 or 2. m is 2 or 3, and n is 1 or 3.
R12、R13はB成分中のリン含有量を適正に保持し、難燃性を好適に発現すると同時に、組成物の結晶性を好適に発現するため、炭素数の平均値が1〜10の範囲にある直鎖または分岐のアルキル基、シクロアルキル基、アリール基またはアラルキル基が好適に選択される。なかでもアルキル基、アリール基が好適に選択される。具体的には、例えばメチル基、エチル基、n−プロピル基、イソプロピル基、n−ブチル基、tert−ブチル基、n−ペンチル基あるいはフェニル基が好適に例示される。 R 12 and R 13 appropriately maintain the phosphorus content in the component B, and preferably exhibit flame retardancy, and at the same time, preferably exhibit the crystallinity of the composition. A linear or branched alkyl group, cycloalkyl group, aryl group or aralkyl group in the range of is preferably selected. Of these, an alkyl group and an aryl group are preferably selected. Specifically, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, an n-pentyl group, or a phenyl group is preferably exemplified.
R13はB成分中のリン含有量を適正に保持し、難燃性を好適に発現すると同時に、組成物の結晶性を好適に発現するため、炭素数が1〜10の範囲にある直鎖または分岐のアルキレン基、シクロアルキレン基、アリーレン基、アルキレンアリーレン基またはシクロアルキレンアリーレン基が好適に選択される。 R 13 appropriately retains the phosphorus content in the B component, and preferably exhibits flame retardancy, and at the same time, preferably exhibits the crystallinity of the composition. Therefore, R 13 is a straight chain having 1 to 10 carbon atoms. Alternatively, a branched alkylene group, cycloalkylene group, arylene group, alkylene arylene group or cycloalkylene arylene group is preferably selected.
具体的には例えばメチレン基、エチレン基、メチルエタン−1,3−ジイル基、プロパン−1,3−ジイル基、2,2−ジメチルプロパン−1,3−ジイル基、ブタン−1,4−ジイル基、オクタン−1,8−ジイル基、フェニレン基、ナフチレン基、エチルフェニレン基、tert−ブチルフェニレン基、メチルナフチレン基、エチルナフチレン基、フェニレンメチレン基、フェニレンエチレン基、フェニレンプロピレン基、フェニレンブチレン基等が例示される。 Specifically, for example, methylene group, ethylene group, methylethane-1,3-diyl group, propane-1,3-diyl group, 2,2-dimethylpropane-1,3-diyl group, butane-1,4-diyl Group, octane-1,8-diyl group, phenylene group, naphthylene group, ethylphenylene group, tert-butylphenylene group, methylnaphthylene group, ethylnaphthylene group, phenylenemethylene group, phenyleneethylene group, phenylenepropylene group, phenylenebutylene group Etc. are exemplified.
Mは、Mg、Ca、Al、Zn、Fe、Zr、Ce、Bi、Sr、Mn、Li、Na、Kまたはプロトン化した窒素塩基を表す。Mが複数ある場合には、各々独立にこれらから選ばれる。プロトン化した窒素塩基としては、アミド基、アンモニウム基、アルキルアンモニウム基あるいはメラミン由来の基が挙げられる。本発明の組成物の難燃性、結晶性、成形性等を向上させるため、MはMg、Ca、Al、Znおよびアミド基、アンモニウム基、アルキルアンモニウム基あるいはメラミン由来の基の群より選択される。中でもAlがもっとも好適に選択される。)
式(8)および(9)で表されるホスフィン酸塩を併用する場合、(8)/(9)の重量比は10/90〜30/70の範囲が好適に選択される。
M represents Mg, Ca, Al, Zn, Fe, Zr, Ce, Bi, Sr, Mn, Li, Na, K, or a protonated nitrogen base. When there are a plurality of M, each is independently selected. Examples of protonated nitrogen bases include amide groups, ammonium groups, alkylammonium groups, and melamine-derived groups. In order to improve the flame retardancy, crystallinity, moldability, etc. of the composition of the present invention, M is selected from the group of Mg, Ca, Al, Zn and groups derived from amide groups, ammonium groups, alkylammonium groups or melamines. The Of these, Al is most preferably selected. )
When the phosphinic acid salts represented by the formulas (8) and (9) are used in combination, the weight ratio of (8) / (9) is preferably selected in the range of 10/90 to 30/70.
(窒素系難燃剤:G−2成分)
本発明で用いられる窒素系難燃剤(G−2成分)は、トリアジン骨格を含む窒素系難燃剤であり、リン系難燃剤の難燃性を相乗的に増大させる剤であり、下記式(10)および(11)からなる群より選ばれる少なくとも一種が適用される。
(Nitrogen flame retardant: G-2 component)
The nitrogen-based flame retardant (G-2 component) used in the present invention is a nitrogen-based flame retardant containing a triazine skeleton, and is an agent that synergistically increases the flame retardancy of a phosphorus-based flame retardant. And at least one selected from the group consisting of (11).
式中、R14〜R16は各々独立に、水素原子、炭素数1〜8のアルキル基、炭素数5〜16のシクロアルキル基、(これらは置換されていないか、水酸基または炭素数1〜4のヒドロキシアルキル基によって置換されている。)、炭素数2〜8のアルケニル基、炭素数1〜8のアルコキシ基、アシル基、アシルオキシ基、炭素数6〜12のアリール基、−O−RA、−N(RA)(RB)またはN−脂環式もしくはN−芳香族の−N(RA)RBで表される基である。ここにおいて、RAおよびRBは、水素原子、炭素数1〜8のアルキル基、炭素数5〜16の−シクロアルキル基(これらは置換されていないか、ヒドロキシル基または炭素数1〜4のヒドロキシアルキル官能基によって置換されている。)、炭素数2〜8のアルケニル基、炭素数1〜8のアルコキシ基、アシル基、アシルオキシ基または炭素数6〜12のアリール基である。 In the formula, each of R 14 to R 16 independently represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 5 to 16 carbon atoms, (these are not substituted, hydroxyl groups or 1 to 4), an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an acyl group, an acyloxy group, an aryl group having 6 to 12 carbon atoms, -O-RA , -N (RA) (RB) or a group represented by N-alicyclic or N-aromatic -N (RA) RB. Here, RA and RB are a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, a -cycloalkyl group having 5 to 16 carbon atoms (these are not substituted, a hydroxyl group or a hydroxyalkyl having 1 to 4 carbon atoms). Substituted with a functional group), an alkenyl group having 2 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, an acyl group, an acyloxy group, or an aryl group having 6 to 12 carbon atoms.
但し、R14〜R16の全てが同時に水素原子であることはなくかつ式(10)においてR14〜R16の全てが同時に−NH2であることはない。Xは、メラミンまたはトリアジン化合物(10)と付加物を形成することができる酸であり、s、tは各々独立に1または2である。 However, not all of R 14 to R 16 are hydrogen atoms at the same time, and all of R 14 to R 16 are not simultaneously —NH 2 in the formula (10). X is an acid capable of forming an adduct with the melamine or triazine compound (10), and s and t are each independently 1 or 2.
式(10)において、R14〜R16の少なくとも一つが炭素数6〜12のアリール基であるとき、リン系難燃剤中でもホスフィン酸塩と配合したとき、より有効に難燃性を高めることができるとともに、本発明組成物の難燃性、結晶性および成形性をより好適に向上させることができる。 In Formula (10), when at least one of R 14 to R 16 is an aryl group having 6 to 12 carbon atoms, the flame retardancy can be more effectively increased when blended with a phosphinate in a phosphorus flame retardant. In addition, the flame retardancy, crystallinity and moldability of the composition of the present invention can be improved more suitably.
また式(11)において、R14〜R16が全て−N(RA)(RB)であるとき、より有効に難燃性を高めることができるとともに、本発明の組成物の難燃性、結晶性および成形性をより好適に向上させることができる
かかる(10)、(11)としては、例えばジメラミンピロホスフェート、メラミンポリホスフェート、メレムポリホスフェート、メラムポリホスフェート、メロンポリホスフェートなどが好適に例示される。
In the formula (11), when all of R 14 to R 16 are —N (RA) (RB), the flame retardancy can be more effectively increased, and the flame retardancy and crystal of the composition of the present invention can be increased. (10) and (11) are preferably exemplified by dimelamine pyrophosphate, melamine polyphosphate, melem polyphosphate, melam polyphosphate, melon polyphosphate, and the like. Is done.
本発明においては、トリアジン骨格を有する窒素系難燃剤に付加的に下記式(12)〜(15)で表される化合物の少なくとも一種を併用することにより本発明の組成物の難燃性を向上させることができる。 In the present invention, the flame retardancy of the composition of the present invention is improved by additionally using at least one compound represented by the following formulas (12) to (15) in addition to the nitrogen-based flame retardant having a triazine skeleton. Can be made.
式中、R7〜R10、R17〜R20は各々独立にR14〜R16で記載した官能基が好適に例示される。例えばトリス(ヒドロキシエチル)イソシアヌレート、アランイン、グリコールウリル、尿素.シアヌレートなどが好適に例示される。かかる剤はトリアジン骨格を含む窒素系難燃剤を基準にして10〜50重量%の範囲で適用される。 In the formula, R 7 to R 10 and R 17 to R 20 are each preferably independently exemplified by the functional groups described as R 14 to R 16 . For example, tris (hydroxyethyl) isocyanurate, allanin, glycoluril, urea. Cyanurate and the like are preferably exemplified. Such an agent is applied in the range of 10 to 50% by weight based on the nitrogen-based flame retardant containing a triazine skeleton.
(水酸化金属化合物系難燃剤:G−3成分)
本発明の水酸化金属化合物系難燃剤(G−3成分)は、水酸化アルミニウム、水酸化マグネシウムおよび水酸化カルシウムであり、組成物の熱安定性が向上のため、純度が高いものが好ましく、特に純度が99.5%以上であるものが好ましい。水酸化金属化合物系難燃剤の純度は公知の方法で測定することができる。例えば、水酸化金属化合物系難燃剤に含まれている不純物の含有量を公知の方法で測定し、全体量から前記不純物の含有量を減じれば、水酸化金属化合物系難燃剤の純度を得ることができる。より具体的には、より具体的には、例えば水酸化アルミニウムの場合、不純物としてはFe2O3、SiO2、T−Na2O、S−Na2O等が挙げられる。Fe2O3の含有量は炭酸ナトリウム−ホウ酸液に融解後、O−フェナントロリン吸光光度法(JIS H 1901)により求められる。SiO2の含有量は炭酸ナトリウム−ホウ酸液に融解後、モリブテン青吸光光度法(JIS H 1901)により求められる。T−Na2Oの含有量は硫酸に融解後、フレーム光度測定法で、S−Na2Oは温水抽出後、フレーム光度測定法で求められる。上記により求められた含有量を水酸化アルミニウムの重量より減じることにより水酸化物の純度を得ることができる。もちろん異なる複数種の水酸化金属化合物系難燃剤を組み合わせて用いることができることは言うまでもない。
(Metal hydroxide compound flame retardant: G-3 component)
The metal hydroxide compound-based flame retardant (G-3 component) of the present invention is aluminum hydroxide, magnesium hydroxide and calcium hydroxide, and preferably has high purity for improving the thermal stability of the composition. Particularly preferred are those having a purity of 99.5% or more. The purity of the metal hydroxide compound flame retardant can be measured by a known method. For example, the content of impurities contained in the metal hydroxide compound flame retardant is measured by a known method, and the purity of the metal hydroxide compound flame retardant is obtained by subtracting the impurity content from the total amount. be able to. More specifically, for example, in the case of aluminum hydroxide, examples of impurities include Fe 2 O 3 , SiO 2 , T—Na 2 O, S—Na 2 O, and the like. The content of Fe 2 O 3 is determined by O-phenanthroline spectrophotometry (JIS H 1901) after melting in a sodium carbonate-boric acid solution. The content of SiO 2 is determined by the molybdenum blue absorptiometry (JIS H 1901) after melting in sodium carbonate-boric acid solution. The content of T-Na 2 O is obtained by a flame photometric method after melting in sulfuric acid, and S-Na 2 O is obtained by a flame photometric method after extraction with hot water. The purity of the hydroxide can be obtained by reducing the content obtained as described above from the weight of aluminum hydroxide. Of course, it is needless to say that different types of metal hydroxide compound flame retardants can be used in combination.
本発明で用いる水酸化金属化合物系難燃剤の形状は特に限定されないが、粒状であることが好ましい。その粒子径は、レーザー回折法により求められる平均粒子径が約100μm以下であることが好ましい。なお、この場合において粒度分布は問わない。成形プロセスにおける射出成形性や混練時の分散性の観点から、平均粒子径は上記範囲が好ましく、上記範囲の中でもより小さい方がより好ましい。なお、もちろん組成物への充填率を高めるために平均粒子径の異なる複数種の水酸化金属化合物系難燃剤を組み合わせて用いることができる。 The shape of the metal hydroxide compound flame retardant used in the present invention is not particularly limited, but is preferably granular. As for the particle diameter, it is preferable that the average particle diameter calculated | required by the laser diffraction method is about 100 micrometers or less. In this case, the particle size distribution does not matter. From the viewpoint of injection moldability in the molding process and dispersibility at the time of kneading, the average particle diameter is preferably in the above range, and more preferably in the above range. Of course, in order to increase the filling rate of the composition, a plurality of kinds of metal hydroxide compound flame retardants having different average particle diameters can be used in combination.
さらに、窒素ガス吸着法により求められるBET比表面積が約5.0m2/g以下の粒子を用いることが好ましい。もちろん組成物への充填率を高めるためにBET比表面積の異なる複数種の水酸化金属化合物系難燃剤を組み合わせて用いることができる。成形性の観点から、BET比表面積は上記範囲が好ましく、上記範囲の中でもより小さい方がより好ましい。 Furthermore, it is preferable to use particles having a BET specific surface area of about 5.0 m 2 / g or less determined by a nitrogen gas adsorption method. Of course, in order to increase the filling rate into the composition, a plurality of types of metal hydroxide compound flame retardants having different BET specific surface areas can be used in combination. From the viewpoint of moldability, the BET specific surface area is preferably in the above range, and a smaller one is more preferable in the above range.
リン系難燃剤(G−1成分)、窒素系難燃剤(G−2成分)、水酸化金属化合物系難燃剤(G−3成分)から選ばれる1種以上の難燃剤(G成分)の含有量は、樹脂成分(A成分)100重量部に対して、1〜100重量部、より好ましくは3〜90重量部、さらに好ましくは5〜80重量部である。含有量が1重量部未満では難燃剤の添加量が少なすぎ、難燃性が得られず、100重量部を超えると耐熱性が悪化して離型性が低下し、寸法安定性が悪化するため、好ましくない。 Inclusion of one or more flame retardants (G component) selected from phosphorus-based flame retardants (G-1 component), nitrogen-based flame retardants (G-2 component), and metal hydroxide compound-based flame retardants (G-3 component) The amount is 1 to 100 parts by weight, more preferably 3 to 90 parts by weight, and still more preferably 5 to 80 parts by weight with respect to 100 parts by weight of the resin component (component A). If the content is less than 1 part by weight, the amount of the flame retardant added is too small and flame retardancy is not obtained. Therefore, it is not preferable.
〈無機充填剤:H成分〉
本発明の組成物は、無機充填剤(H成分)を含有してもよい。無機充填剤合により、機械特性、耐熱性、成形性の優れた組成物を得ることができる。本発明で使用する無機充填剤としては、通常の熱可塑性樹脂の強化に用いられる繊維状、板状、粉末状のものを用いることができる。
<Inorganic filler: H component>
The composition of the present invention may contain an inorganic filler (H component). A composition excellent in mechanical properties, heat resistance and moldability can be obtained by the inorganic filler. As the inorganic filler used in the present invention, a fibrous, plate-like, or powder-like material used for reinforcing ordinary thermoplastic resins can be used.
具体的には例えば、カーボンナノチューブ、ガラス繊維、アスベスト繊維、炭素繊維、グラファイト繊維、金属繊維、チタン酸カリウムウイスカー、ホウ酸アルミニウムウイスカー、マグネシウム系ウイスカー、珪素系ウイスカー、ワラストナイト、イモゴライト、セピオライト、アスベスト、スラグ繊維、ゾノライト、石膏繊維、シリカ繊維、シリカ.アルミナ繊維、ジルコニア繊維、窒化ホウ素繊維、窒化珪素繊維およびホウ素繊維等の繊維状無機充填剤、層状珪酸塩、有機オニウムイオンで交換された層状珪酸塩、ガラスフレーク、非膨潤性雲母、グラファイト、金属箔、セラミックビーズ、タルク、クレイ、マイカ、セリサイト、ゼオライト、ベントナイト、ドロマイト、カオリン、粉末珪酸、長石粉、チタン酸カリウム、シラスバルーン、炭酸カルシウム、炭酸マグネシウム、硫酸バリウム、酸化カルシクム、酸化アルミニウム、酸化チタン、珪酸アルミニウム、酸化ケイ素、石膏、ノバキュライト、ドーソナイトおよび白土フラーレンなどのカーボンナノ粒子等の板状や粒子状の無機充填剤が挙げられる。 Specifically, for example, carbon nanotube, glass fiber, asbestos fiber, carbon fiber, graphite fiber, metal fiber, potassium titanate whisker, aluminum borate whisker, magnesium whisker, silicon whisker, wollastonite, imogolite, sepiolite, Asbestos, slag fiber, zonolite, gypsum fiber, silica fiber, silica. Fibrous inorganic fillers such as alumina fiber, zirconia fiber, boron nitride fiber, silicon nitride fiber and boron fiber, layered silicate, layered silicate exchanged with organic onium ions, glass flake, non-swellable mica, graphite, metal Foil, ceramic beads, talc, clay, mica, sericite, zeolite, bentonite, dolomite, kaolin, powdered silicic acid, feldspar powder, potassium titanate, shirasu balloon, calcium carbonate, magnesium carbonate, barium sulfate, calcium oxide, aluminum oxide, Examples thereof include plate-like and particulate inorganic fillers such as carbon nanoparticles such as titanium oxide, aluminum silicate, silicon oxide, gypsum, novaculite, dawsonite, and white clay fullerene.
層状珪酸塩の具体例としては、モンモリロナイト、バイデライト、ノントロナイト、サポナイト、ヘクトライト、ソーコナイト等のスメクタイト系粘土鉱物、バーミキュライト、ハロサイト、カネマイト、ケニヤイト等の各種粘土鉱物、Li型フッ素テニオライト、Na型フッ素テニオライト、LI型四珪素フッ素雲母、Na型四珪素フッ素雲母等の膨潤性雲母等が挙げられる。これらは天然のものであっても合成のものであって良い。これらのなかでモンモリロナイト、ヘクトライト等のスメクタイト系粘土鉱物やLi型フッ素テニオライト、Na型四珪素フッ素雲母等の膨潤性合成雲母が好ましい。 Specific examples of layered silicates include smectite clay minerals such as montmorillonite, beidellite, nontronite, saponite, hectorite, and soconite, various clay minerals such as vermiculite, halosite, kanemite, and kenyanite, Li-type fluorine teniolite, Na Swellable mica, such as fluorinated teniolite, LI-type tetrasilicon fluorine mica, and Na-type tetrasilicon fluorine mica. These may be natural or synthetic. Among these, smectite clay minerals such as montmorillonite and hectorite, and swellable synthetic mica such as Li type fluorine teniolite and Na type tetrasilicon fluorine mica are preferable.
これらの無機充填剤のなかでは繊維状もしくは板状の無機充填剤が好ましく、特にガラス繊維、ワラステナイト、ホウ酸アルミニウムウイスカー、チタン酸カリウムウイスカー、マイカ、およびカオリン、陽イオン交換された層状珪酸塩が好ましい。また繊維状充填剤のアスペクト比は5以上であることが好ましく、10以上でありことがさらに好ましく、20以上であることがさらに好ましい。 Among these inorganic fillers, fibrous or plate-like inorganic fillers are preferable, and glass fiber, wollastonite, aluminum borate whisker, potassium titanate whisker, mica, and kaolin, a cation-exchanged layered silicate. Is preferred. The aspect ratio of the fibrous filler is preferably 5 or more, more preferably 10 or more, and further preferably 20 or more.
かかる充填剤はエチレン/酢酸ビニル共重合体等の熱可塑性樹脂やエポキシ樹脂等の熱硬化性樹脂で被覆または収束処理されていてもよく、またアミノシランやエポキシシラン等のカップリング剤で処理されていても良い。 Such a filler may be coated or converged with a thermoplastic resin such as an ethylene / vinyl acetate copolymer or a thermosetting resin such as an epoxy resin, or may be treated with a coupling agent such as aminosilane or epoxysilane. May be.
無機充填剤(H成分)の含有量は、樹脂成分(A成分)100重量部に対し、好ましくは0.05〜100重量部、より好ましくは0.5〜100重量部、さらに好ましくは1〜50重量部、特に好ましくは1〜30重量部、最も好ましくは1〜20重量部である。かかる配合量が0.05重量部より小さい場合には、補強効果が十分でなく、また100重量部を超えると、成形品外観の悪化や押出性時のストランド切れなどを起こすため好ましくない。 The content of the inorganic filler (H component) is preferably 0.05 to 100 parts by weight, more preferably 0.5 to 100 parts by weight, further preferably 1 to 100 parts by weight of the resin component (component A). 50 parts by weight, particularly preferably 1 to 30 parts by weight, most preferably 1 to 20 parts by weight. When the blending amount is less than 0.05 parts by weight, the reinforcing effect is not sufficient, and when it exceeds 100 parts by weight, the appearance of the molded product is deteriorated or the strand breaks at the time of extrudability.
〈光安定剤〉
本発明の組成物は光安定剤を含有していてもよい。光安定剤としては、具体的には例えば、ベンゾフェノン系化合物、ベンゾトリアゾール系化合物、芳香族ベンゾエート系化合物、蓚酸アニリド系化合物、シアノアクリレート系化合物およびヒンダードアミン系化合物等を挙げることができる。
<Light stabilizer>
The composition of the present invention may contain a light stabilizer. Specific examples of the light stabilizer include benzophenone compounds, benzotriazole compounds, aromatic benzoate compounds, oxalic acid anilide compounds, cyanoacrylate compounds, hindered amine compounds, and the like.
ベンゾフェノン系化合物としては、ベンゾフェノン、2,4−ジヒドロキシベンゾフェノン、2,2’−ジヒドロキシベンゾフェノン、2,2’,4,4’−テトラヒドロキシベンゾフェノン、2−ヒドロキシ−4−メトキシベンゾフェノン、2,2’−ジヒドロキシ−4,4’−ジメトキシベンゾフェノン、2,2’−ジヒドロキシ−4,4’−ジメトキシ−5−スルホベンゾフェノン、2−ヒドロキシ−4−オクトキシベンゾフェノン、2−ヒドロキシ−4−ドデシロキシベンゾフェノン、2−ヒドロキシ−4−オクトキシベンゾフェノン、2−ヒドロキシ−4−メトキシ−5−スルホベンゾフェノン、5−クロロ−2−ヒドロキシベンゾフェノン、2−ヒドロキシ−4−オクトキシベンゾフェノン、2−ヒドロキシ−4−メトキシ−2’−カルボキシベンゾフェノン、2−ヒドロキシ−4−(2−ヒドロキシ−3−メチル−アクリロキシイソプロポキシ)ベンゾフェノン等が挙げられる。 Examples of the benzophenone compounds include benzophenone, 2,4-dihydroxybenzophenone, 2,2′-dihydroxybenzophenone, 2,2 ′, 4,4′-tetrahydroxybenzophenone, 2-hydroxy-4-methoxybenzophenone, 2,2 ′. -Dihydroxy-4,4'-dimethoxybenzophenone, 2,2'-dihydroxy-4,4'-dimethoxy-5-sulfobenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-dodecyloxybenzophenone 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-methoxy-5-sulfobenzophenone, 5-chloro-2-hydroxybenzophenone, 2-hydroxy-4-octoxybenzophenone, 2-hydroxy-4-methoxy -2 - carboxy benzophenone, 2-hydroxy-4- (2-hydroxy-3-methyl - acryloxy-isopropoxyphenyl) benzophenone.
ベンゾトリアゾール系化合物としては、2−(5−メチル−2−ヒドロキシフェニル)ベンゾトリアゾール、2−(3,5−ジ−t−ブチル−2−ヒドロキシフェニル)ベンゾトリアゾール、2−(3,5−ジ−t−アミル−2−ヒドロキシフェニル)ベンゾトリアゾール、2−(3’,5’−ジ−t−ブチル−4’−メチル−2’−ヒドロキシフェニル)ベンゾトリアゾール、2−(3,5−ジ−t−アミル−2−ヒドロキシフェニル)−5−クロロベンゾトリアゾール、2−(5−t−ブチル−2−ヒドロキシフェニル)ベンゾトリアゾール、2−[2’−ヒドロキシ−3’,5’−ビス(α,α−ジメチルベンジル)フェニル]ベンゾトリアゾール、2−[2’−ヒドロキシ−3’,5’−ビス(α,α−ジメチルベンジル)フェニル]−2H−ベンゾトリアゾール、2−(4’−オクトキシ−2’−ヒドロキシフェニル)ベンゾトリアゾール等が挙げられる。 Examples of the benzotriazole compound include 2- (5-methyl-2-hydroxyphenyl) benzotriazole, 2- (3,5-di-t-butyl-2-hydroxyphenyl) benzotriazole, 2- (3,5- Di-t-amyl-2-hydroxyphenyl) benzotriazole, 2- (3 ′, 5′-di-t-butyl-4′-methyl-2′-hydroxyphenyl) benzotriazole, 2- (3,5- Di-t-amyl-2-hydroxyphenyl) -5-chlorobenzotriazole, 2- (5-t-butyl-2-hydroxyphenyl) benzotriazole, 2- [2′-hydroxy-3 ′, 5′-bis (Α, α-dimethylbenzyl) phenyl] benzotriazole, 2- [2′-hydroxy-3 ′, 5′-bis (α, α-dimethylbenzyl) phenyl] 2H- benzotriazole, 2- (4'-octoxy-2'-hydroxyphenyl) benzotriazole.
芳香族ベンゾエート系化合物としては、p−t−ブチルフェニルサリシレート、p−オクチルフェニルサリシレート等のアルキルフェニルサリシレート類が挙げられる。 Examples of the aromatic benzoate compounds include alkylphenyl salicylates such as pt-butylphenyl salicylate and p-octylphenyl salicylate.
蓚酸アニリド系化合物としては、2−エトキシ−2’−エチルオキザリックアシッドビスアニリド、2−エトキシ−5−t−ブチル−2’−エチルオキザリックアシッドビスアニリド、2−エトキシ−3’−ドデシルオキザリックアシッドビスアニリド等が挙げられる。 Examples of oxalic acid anilide compounds include 2-ethoxy-2′-ethyloxalic acid bisanilide, 2-ethoxy-5-tert-butyl-2′-ethyloxalic acid bisanilide, and 2-ethoxy-3′-. Examples include dodecyl oxalic acid bisanilide.
シアノアクリレート系化合物としては、エチル−2−シアノ−3,3’−ジフェニルアクリレート、2−エチルヘキシル−シアノ−3,3’−ジフェニルアクリレート等が挙げられる。 Examples of the cyanoacrylate compound include ethyl-2-cyano-3,3'-diphenyl acrylate, 2-ethylhexyl-cyano-3,3'-diphenyl acrylate, and the like.
ヒンダードアミン系化合物としては、4−アセトキシ−2,2,6,6−テトラメチルピペリジン、4−ステアロイルオキシ−2,2,6,6−テトラメチルピペリジン、4−アクリロイルオキシ−2,2,6,6−テトラメチルピペリジン、4−(フェニルアセトキシ)−2,2,6,6−テトラメチルピペリジン、4−ベンゾイルオキシ−2,2,6,6−テトラメチルピペリジン、4−メトキシ−2,2,6,6−テトラメチルピペリジン、4−オクタデシルオキシ−2,2,6,6−テトラメチルピペリジン、4−シクロヘキシルオキシ−2,2,6,6−テトラメチルピペリジン、4−ベンジルオキシ−2,2,6,6−テトラメチルピペリジン、4−フェノキシ−2,2,6,6−テトラメチルピペリジン、4−(エチルカルバモイルオキシ)−2,2,6,6−テトラメチルピペリジン、4−(シクロヘキシルカルバモイルオキシ)−2,2,6,6−テトラメチルピペリジン、4−(フェニルカルバモイルオキシ)−2,2,6,6−テトラメチルピペリジン、ビス(2,2,6,6−テトラメチル−4−ピペリジル)カーボネート、ビス(2,2,6,6−テトラメチル−4−ピペリジル)オギザレート、ビス(2,2,6,6−テトラメチル−4−ピペリジル)マロネート、ビス(2,2,6,6−テトラメチル−4−ピペリジル)セバケート、ビス(2,2,6,6−テトラメチルピ−4−ペリジル)アジペート、ビス(2,2,6,6−テトラメチルピ−4−ペリジル)テレフタレート、1,2−ビス(2,2,6,6−テトラメチルピ−4−ペリジルオキシ)−エタン、α,α’−ビス(2,2,6,6−テトラメチル−4−ピペリジルオキシ)−p−キシレン、ビス(2,2,6,6−テトラメチル−4−ピペリジル)−トリレン−2,4−ジカルバメート、ビス(2,2,6,6−テトラメチル−4−ピペリジル)−ヘキサメチレン−1,6−ジカルバメート、トリス(2,2,6,6−テトラメチル−4−ピペリジル)−ベンゼン−1,3,5−トリカルボキシレート、トリス(2,2,6,6−テトラメチル−4−ピペリジル)−ベンゼン−1,3,4−トリカルボキシレート、1−「2−{3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオニルオキシ}−2,2,6,6−テトラメチルピペリジン、1,2,3,4−ブタンテトラカルボン酸と1,2,2,6,6−ペンタメチル−4−ピペリジノールとβ,β,β’,β’−テトラメチル−3,9−[2,4,8,10−テトラオキサスピロ(5,5)ウンデカンン]ジメタノルとの縮合物等を挙げることができる。
安定剤の含有量は、樹脂成分(A成分)100重量部当たり、好ましくは0.01〜3重量部、より好ましくは0.03〜2重量部である。
Examples of hindered amine compounds include 4-acetoxy-2,2,6,6-tetramethylpiperidine, 4-stearoyloxy-2,2,6,6-tetramethylpiperidine, 4-acryloyloxy-2,2,6, 6-tetramethylpiperidine, 4- (phenylacetoxy) -2,2,6,6-tetramethylpiperidine, 4-benzoyloxy-2,2,6,6-tetramethylpiperidine, 4-methoxy-2,2, 6,6-tetramethylpiperidine, 4-octadecyloxy-2,2,6,6-tetramethylpiperidine, 4-cyclohexyloxy-2,2,6,6-tetramethylpiperidine, 4-benzyloxy-2,2 , 6,6-tetramethylpiperidine, 4-phenoxy-2,2,6,6-tetramethylpiperidine, 4- (ethylcarba Yloxy) -2,2,6,6-tetramethylpiperidine, 4- (cyclohexylcarbamoyloxy) -2,2,6,6-tetramethylpiperidine, 4- (phenylcarbamoyloxy) -2,2,6,6 -Tetramethylpiperidine, bis (2,2,6,6-tetramethyl-4-piperidyl) carbonate, bis (2,2,6,6-tetramethyl-4-piperidyl) oxalate, bis (2,2,6 , 6-Tetramethyl-4-piperidyl) malonate, bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (2,2,6,6-tetramethylpi-4-peridyl) adipate, bis (2,2,6,6-tetramethylpi-4-peridyl) terephthalate, 1,2-bis (2,2,6,6-tetramethylpi-4-peridylo) Cis) -ethane, α, α′-bis (2,2,6,6-tetramethyl-4-piperidyloxy) -p-xylene, bis (2,2,6,6-tetramethyl-4-piperidyl) -Tolylene-2,4-dicarbamate, bis (2,2,6,6-tetramethyl-4-piperidyl) -hexamethylene-1,6-dicarbamate, tris (2,2,6,6-tetramethyl -4-piperidyl) -benzene-1,3,5-tricarboxylate, tris (2,2,6,6-tetramethyl-4-piperidyl) -benzene-1,3,4-tricarboxylate, 1- “2- {3- (3,5-di-t-butyl-4-hydroxyphenyl) propionyloxy} -2,2,6,6-tetramethylpiperidine, 1,2,3,4-butanetetracarboxylic acid And 1,2,2,6,6- Examples include condensates of n-methyl-4-piperidinol and β, β, β ′, β′-tetramethyl-3,9- [2,4,8,10-tetraoxaspiro (5,5) undecane] dimethanol. be able to.
The content of the stabilizer is preferably 0.01 to 3 parts by weight, more preferably 0.03 to 2 parts by weight per 100 parts by weight of the resin component (component A).
〈結晶化促進剤〉
本発明の組成物は結晶化促進剤を含有していてもよい。結晶化促進剤を含有することで、リン酸エステル金属塩(C成分)の作用を一層増強することができ、機械的特性、耐熱性、および成形性に優れた成形品を得ることができる。
即ち結晶化促進剤の適用により、樹脂成分(A成分)の成形性、結晶性が向上し、通常の射出成形においても十分に結晶化し耐熱性、耐湿熱安定性に優れた成形品を得ることができる。加えて、成形品を製造する製造時間を大幅に短縮でき、その経済的効果は大きい。
<Crystal Accelerator>
The composition of the present invention may contain a crystallization accelerator. By containing a crystallization accelerator, the action of the phosphate ester metal salt (component C) can be further enhanced, and a molded product having excellent mechanical properties, heat resistance, and moldability can be obtained.
That is, by applying the crystallization accelerator, the moldability and crystallinity of the resin component (component A) are improved, and a molded product that is sufficiently crystallized even in normal injection molding and has excellent heat resistance and moist heat resistance is obtained. Can do. In addition, the manufacturing time for manufacturing the molded product can be greatly shortened, and the economic effect is great.
結晶化促進剤として、無機系の結晶化核剤および有機系の結晶化核剤のいずれをも使用することができる。
無機系の結晶化核剤として、タルク、カオリン、シリカ、合成マイカ、クレイ、ゼオライト、グラファイト、カーボンブラック、酸化亜鉛、酸化マグネシウム、酸化チタン、炭酸カルシウム、硫酸カルシウム、硫酸バリウム、硫化カルシウム、窒化ホウ素、モンモリロナイト、酸化ネオジム、酸化アルミニウム、フェニルフォスフォネート金属塩等が挙げられる。これらの無機系の結晶化核剤は組成物中での分散性およびその効果を高めるために、各種分散助剤で処理され、一次粒子径が0.01〜0.5μm程度の高度に分散状態にあるものが好ましい。
As the crystallization accelerator, either an inorganic crystallization nucleating agent or an organic crystallization nucleating agent can be used.
As inorganic crystallization nucleating agents, talc, kaolin, silica, synthetic mica, clay, zeolite, graphite, carbon black, zinc oxide, magnesium oxide, titanium oxide, calcium carbonate, calcium sulfate, barium sulfate, calcium sulfide, boron nitride , Montmorillonite, neodymium oxide, aluminum oxide, phenylphosphonate metal salt and the like. These inorganic crystallization nucleating agents are treated with various dispersing aids in order to enhance the dispersibility in the composition and the effect thereof, and are in a highly dispersed state with a primary particle size of about 0.01 to 0.5 μm. Are preferred.
有機系の結晶化核剤としては、安息香酸カルシウム、安息香酸ナトリウム、安息香酸リチウム、安息香酸カリウム、安息香酸マグネシウム、安息香酸バリウム、蓚酸カルシウム、テレフタル酸ジナトリウム、テレフタル酸ジリチウム、テレフタル酸ジカリウム、ラウリン酸ナトリウム、ラウリン酸カリウム、ミリスチン酸ナトリウム、ミリスチン酸カリウム、ミリスチン酸カルシウム、ミリスチン酸バリウム、オクタコ酸ナトリウム、オクタコ酸カルシウム、ステアリン酸ナトリウム、ステアリン酸カリウム、ステアリン酸リチウム、ステアリン酸カルシウム、ステアリン酸マグネシウム、ステアリン酸バリウム、モンタン酸ナトリウム、モンタン酸カルシウム、トルイル酸ナトリウム、サリチル酸ナトリウム、サリチル酸カリウム、サリチル酸亜鉛、アルミニウムジベンゾエート、β−ナフトエ酸ナトリウム、β−ナフトエ酸カリウム、シクロヘキサンカルボン酸ナトリウム等の有機カルボン酸金属塩、p−トルエンスルホン酸ナトリウム、スルホイソフタル酸ナトリウム等の有機スルホン酸金属塩が挙げられる。 Organic crystallization nucleating agents include calcium benzoate, sodium benzoate, lithium benzoate, potassium benzoate, magnesium benzoate, barium benzoate, calcium oxalate, disodium terephthalate, dilithium terephthalate, dipotassium terephthalate, Sodium laurate, potassium laurate, sodium myristate, potassium myristate, calcium myristate, barium myristate, sodium octacolate, calcium octacolate, sodium stearate, potassium stearate, lithium stearate, calcium stearate, magnesium stearate , Barium stearate, sodium montanate, calcium montanate, sodium toluate, sodium salicylate, potassium salicylate, salicy Organic carboxylic acid metal salts such as zinc acid, aluminum dibenzoate, β-naphthoic acid sodium, β-naphthoic acid potassium, sodium cyclohexanecarboxylic acid and the like, and organic sulfonic acid metal salts such as sodium p-toluenesulfonate and sodium sulfoisophthalate. Can be mentioned.
また、ステアリン酸アミド、エチレンビスラウリン酸アミド、パルミチン酸アミド、ヒドロキシステアリン酸アミド、エルカ酸アミド、トリメシン酸トリス(t−ブチルアミド)等の有機カルボン酸アミド、低密度ポリエチレン、高密度ポリエチレン、ポリイソプロピレン、ポリブテン、ポリ−4−メチルペンテン、ポリ−3−メチルブテン−1、ポリビニルシクロアルカン、ポリビニルトリアルキルシラン、高融点ポリ乳酸、エチレン−アクリル酸コポマーのナトリウム塩、スチレン−無水マレイン酸コポリマーのナトリウム塩(いわゆるアイオノマー)、ベンジリデンソルビトールおよびその誘導体、例えばジベンジリデンソルビトール等が挙げられる。 In addition, stearic acid amide, ethylene bislauric acid amide, palmitic acid amide, hydroxy stearic acid amide, erucic acid amide, trimesic acid tris (t-butylamide) and other organic carboxylic acid amides, low density polyethylene, high density polyethylene, polyiso Propylene, polybutene, poly-4-methylpentene, poly-3-methylbutene-1, polyvinylcycloalkane, polyvinyltrialkylsilane, high melting point polylactic acid, sodium salt of ethylene-acrylic acid copolymer, sodium of styrene-maleic anhydride copolymer Examples thereof include salts (so-called ionomers), benzylidene sorbitol and derivatives thereof such as dibenzylidene sorbitol.
これらのなかでタルク、および有機カルボン酸金属塩から選択された少なくとも1種が好ましく使用される。本発明で使用する結晶化核剤は1種のみでもよく、2種以上を併用しても良い。
結晶化促進剤の含有量は、樹脂成分(A成分)100重量部当たり、好ましくは0.01〜30重量部、より好ましくは0.05〜20重量部である。
Among these, at least one selected from talc and organic carboxylic acid metal salts is preferably used. Only one type of crystallization nucleating agent may be used in the present invention, or two or more types may be used in combination.
The content of the crystallization accelerator is preferably 0.01 to 30 parts by weight, more preferably 0.05 to 20 parts by weight per 100 parts by weight of the resin component (component A).
〈有機充填剤〉
本発明の組成物は、有機充填剤を含有することができる。有機充填剤を含有することで、機械的特性、耐熱性および成形性に優れた組成物を得ることができる。
有機充填剤として、籾殻、木材チップ、おから、古紙粉砕材、衣料粉砕材等のチップ状のもの、綿繊維、麻繊維、竹繊維、木材繊維、ケナフ繊維、ジュート繊維、バナナ繊維、ココナツ繊維等の植物繊維もしくはこれらの植物繊維から加工されたパルプやセルロース繊維および絹、羊毛、アンゴラ、カシミヤ、ラクダ等の動物繊維等の繊維状のもの、ポリエステル繊維、ナイロン繊維、アクリル繊維等の合成繊維、紙粉、木粉、セルロース粉末、籾殻粉末、果実殻粉末、キチン粉末、キトサン粉末、タンパク質、澱粉等の粉末状のものが挙げられる。成形性の観点から紙粉、木粉、竹粉、セルロース粉末、ケナフ粉末、籾殻粉末、果実殻粉末、キチン粉末、キトサン粉末、タンパク質粉末、澱粉等の粉末状のものが好ましく、紙粉、木粉、竹粉、セルロース粉末、ケナフ粉末が好ましい。紙粉、木粉がより好ましい。特に紙粉が好ましい。
<Organic filler>
The composition of the present invention may contain an organic filler. By containing the organic filler, a composition excellent in mechanical properties, heat resistance and moldability can be obtained.
Organic fillers such as rice husks, wood chips, okara, waste paper ground materials, clothing ground materials, cotton fibers, hemp fibers, bamboo fibers, wood fibers, kenaf fibers, jute fibers, banana fibers, coconut fibers Plant fibers such as pulp, cellulose fibers processed from these plant fibers and fibrous fibers such as animal fibers such as silk, wool, Angola, cashmere, camel, etc., synthetic fibers such as polyester fibers, nylon fibers and acrylic fibers , Paper powder, wood powder, cellulose powder, rice husk powder, fruit husk powder, chitin powder, chitosan powder, protein, starch and the like. From the viewpoint of moldability, powdery materials such as paper powder, wood powder, bamboo powder, cellulose powder, kenaf powder, rice husk powder, fruit husk powder, chitin powder, chitosan powder, protein powder, and starch are preferred. Powder, bamboo powder, cellulose powder and kenaf powder are preferred. Paper powder and wood powder are more preferable. Paper dust is particularly preferable.
これら有機充填剤は天然物から直接採取したものを使用してもよいが、古紙、廃材木および古衣等の廃材をリサイクルしたものを使用してもよい。また木材として、松、杉、檜、もみ等の針葉樹材、ブナ、シイ、ユーカリ等の広葉樹材等が好ましい。 These organic fillers may be those directly collected from natural products, but may also be those obtained by recycling waste materials such as waste paper, waste wood and old clothes. The wood is preferably a softwood material such as pine, cedar, oak or fir, or a hardwood material such as beech, shii or eucalyptus.
紙粉は成形性の観点から接着剤、取り分け紙を加工する際に通常使用される酢酸ビニル樹脂系エマルジョンやアクリル樹脂系エマルジョン等のエマルジョン系接着剤、ポリビニルアルコール系接着剤、ポリアミド系接着剤等のホットメルト接着剤等を含むものが好ましく例示される。 Paper powder is an adhesive from the viewpoint of moldability, especially emulsion-based adhesives such as vinyl acetate resin-based emulsions and acrylic resin-based emulsions when processing paper, polyvinyl alcohol-based adhesives, polyamide-based adhesives, etc. Preferred examples include those containing a hot melt adhesive.
本発明において有機充填剤の含有量は、成形性および耐熱性の観点から、樹脂成分(A成分)100重量部当たり、好ましくは1〜300重量部、より好ましくは5〜200重量部、さらに好ましくは10〜150重量部、特に好ましくは15〜100重量部である。 In the present invention, the content of the organic filler is preferably 1 to 300 parts by weight, more preferably 5 to 200 parts by weight, and still more preferably 100 parts by weight of the resin component (component A) from the viewpoints of moldability and heat resistance. Is 10 to 150 parts by weight, particularly preferably 15 to 100 parts by weight.
〈離型剤〉
本発明の組成物は離型剤を含有していてもよい。離型剤として具体的には、脂肪酸、脂肪酸金属塩、オキシ脂肪酸、パラフィン、低分子量のポリオレフィン、脂肪酸アミド、アルキレンビス脂肪酸アミド、脂肪族ケトン、脂肪酸部分鹸化エステル、脂肪酸低級アルコールエステル、脂肪酸多価アルコールエステル、脂肪酸ポリグリコールエステル、変性シリコーン等を挙げることができる。これらを配合することで機械特性、成形性、耐熱性に優れたポリ乳酸成形品を得ることができる。
<Release agent>
The composition of the present invention may contain a release agent. Specific examples of release agents include fatty acids, fatty acid metal salts, oxy fatty acids, paraffins, low molecular weight polyolefins, fatty acid amides, alkylene bis fatty acid amides, aliphatic ketones, fatty acid partial saponified esters, fatty acid lower alcohol esters, fatty acid polyvalents. Examples include alcohol esters, fatty acid polyglycol esters, and modified silicones. By blending these, a polylactic acid molded product excellent in mechanical properties, moldability, and heat resistance can be obtained.
脂肪酸としては炭素数6〜40のものが好ましく、具体的には、オレイン酸、ステアリン酸、ラウリン酸、ヒドロキシステアリン酸、ベヘン酸、アラキドン酸、リノール酸、リノレン酸、リシノール酸、パルミチン酸、モンタン酸およびこれらの混合物等が挙げられる。脂肪酸金属塩としては炭素数6〜40の脂肪酸のアルカリ(土類)金属塩が好ましく、具体的にはステアリン酸カルシウム、モンタン酸ナトリウム、モンタン酸カルシウム、等が挙げられる。 Fatty acids having 6 to 40 carbon atoms are preferred. Specifically, oleic acid, stearic acid, lauric acid, hydroxystearic acid, behenic acid, arachidonic acid, linoleic acid, linolenic acid, ricinoleic acid, palmitic acid, montan Examples thereof include acids and mixtures thereof. The fatty acid metal salt is preferably an alkali (earth) metal salt of a fatty acid having 6 to 40 carbon atoms, and specific examples include calcium stearate, sodium montanate, calcium montanate, and the like.
オキシ脂肪酸としては1,2−オキシステリン酸、等が挙げられる。パラフィンとしては炭素数18以上のものが好ましく、流動パラフィン、天然パラフィン、マイクロクリスタリンワックス、ペトロラクタム等が挙げられる。 Examples of the oxy fatty acid include 1,2-oxysteric acid. Paraffin having 18 or more carbon atoms is preferable, and examples thereof include liquid paraffin, natural paraffin, microcrystalline wax, petrolactam and the like.
低分子量のポリオレフィンとしては例えば分子量5000以下のものが好ましく、具体的にはポリエチレンワックス、マレイン酸変性ポリエチレンワックス、酸化タイプポリエチレンワックス、塩素化ポリエチレンワックス、ポリプロピレンワックス等が挙げられる。脂肪酸アミドとしては炭素数6以上のものが好ましく、具体的にはオレイン酸アミド、エルカ酸アミド、ベヘン酸アミド等が挙げられる。 As the low molecular weight polyolefin, for example, those having a molecular weight of 5000 or less are preferable, and specific examples include polyethylene wax, maleic acid-modified polyethylene wax, oxidized type polyethylene wax, chlorinated polyethylene wax, and polypropylene wax. As the fatty acid amide, those having 6 or more carbon atoms are preferable, and specific examples include oleic acid amide, erucic acid amide, and behenic acid amide.
アルキレンビス脂肪酸アミドとしては炭素数6以上のものが好ましく、具体的にはメチレンビスステアリン酸アミド、エチレンビスステアリン酸アミド、N,N−ビス(2−ヒドロキシエチル)ステアリン酸アミド等が挙げられる。脂肪族ケトンとしては炭素数6以上のものが好ましく、高級脂肪族ケトン等が挙げられる。 The alkylene bis fatty acid amide is preferably one having 6 or more carbon atoms, and specifically includes methylene bis stearic acid amide, ethylene bis stearic acid amide, N, N-bis (2-hydroxyethyl) stearic acid amide and the like. As the aliphatic ketone, those having 6 or more carbon atoms are preferable, and examples thereof include higher aliphatic ketones.
脂肪酸部分鹸化エステルとしてはモンタン酸部分鹸化エステル等が挙げられる。脂肪酸低級アルコールエステルとしてはステアリン酸エステル、オレイン酸エステル、リノール酸エステル、リノレン酸エステル、アジピン酸エステル、ベヘン酸エステル、アラキドン酸エステル、モンタン酸エステル、イソステアリン酸エステル等が挙げられる。 Examples of the fatty acid partial saponified ester include a montanic acid partial saponified ester. Examples of the fatty acid lower alcohol ester include stearic acid ester, oleic acid ester, linoleic acid ester, linolenic acid ester, adipic acid ester, behenic acid ester, arachidonic acid ester, montanic acid ester, isostearic acid ester and the like.
脂肪酸多価アルコールエステルとしては、グリセロールトリステアレート、グリセロールジステアレート、グリセロールモノステアレート、ペンタエリスルトールテトラステアレート、ペンタエリスルトールトリステアレート、ペンタエリスルトールジミリステート、ペンタエリスルトールものステアレート、ペンタエリスルトールアジペートステアレート、ソルビタンモノベヘネート等が挙げられる。脂肪酸ポリグリコールエステルとしてはポリエチレングリコール脂肪酸エステルやポリプロピレングリコール脂肪酸エステル等が挙げられる。 Examples of fatty acid polyhydric alcohol esters include glycerol tristearate, glycerol distearate, glycerol monostearate, pentaerythritol tetrastearate, pentaerythritol tristearate, pentaerythritol dimyristate, pentaerythritol Examples include tall stearate, pentaerythritol adipate stearate, and sorbitan monobehenate. Examples of fatty acid polyglycol esters include polyethylene glycol fatty acid esters and polypropylene glycol fatty acid esters.
変性シリコーンとしてはポリエーテル変性シリコーン、高級脂肪酸アルコキシ変性シリコーン、高級脂肪酸含有シリコーン、高級脂肪酸エステル変性シリコーン、メタクリル変性シリコーン、フッ素変性シリコーン等が挙げられる。 Examples of the modified silicone include polyether-modified silicone, higher fatty acid alkoxy-modified silicone, higher fatty acid-containing silicone, higher fatty acid ester-modified silicone, methacryl-modified silicone, and fluorine-modified silicone.
そのうち脂肪酸、脂肪酸金属塩、オキシ脂肪酸、脂肪酸エステル、脂肪酸部分鹸化エステル、パラフィン、低分子量ポリオレフィン、脂肪酸アミド、アルキレンビス脂肪酸アミド、が好ましく、脂肪酸部分鹸化エステル、アルキレンビス脂肪酸アミドがより好ましい。なかでもモンタン酸エステル、モンタン酸部分鹸化エステル、ポリエチレンワックッス、酸価ポリエチレンワックス、ソルビタン脂肪酸エステル、エルカ酸アミド、エチレンビスステアリン酸アミドが好ましく、特にモンタン酸部分鹸化エステル、エチレンビスステアリン酸アミドが好ましい。 Of these, fatty acid, fatty acid metal salt, oxy fatty acid, fatty acid ester, fatty acid partial saponified ester, paraffin, low molecular weight polyolefin, fatty acid amide, and alkylene bis fatty acid amide are preferred, and fatty acid partial saponified ester and alkylene bis fatty acid amide are more preferred. Of these, montanic acid ester, montanic acid partial saponified ester, polyethylene wax, acid value polyethylene wax, sorbitan fatty acid ester, erucic acid amide, and ethylene bisstearic acid amide are preferred, and particularly, montanic acid partial saponified ester and ethylene bisstearic acid amide are preferred. preferable.
離型剤は、1種類で用いても良いし2種以上を組み合わせて用いても良い。離型剤の含有量は、樹脂成分(A成分)100重量部に対し、好ましくは0.01〜3重量部、より好ましくは0.03〜2重量部である。 A mold release agent may be used by 1 type and may be used in combination of 2 or more type. The content of the release agent is preferably 0.01 to 3 parts by weight, more preferably 0.03 to 2 parts by weight, with respect to 100 parts by weight of the resin component (component A).
〈帯電防止剤〉
本発明の組成物は帯電防止剤を含有していてもよい。帯電防止剤として、(β−ラウラミドプロピオニル)トリメチルアンモニウムスルフェート、ドデシルベンゼンスルホン酸ナトリウムなどの第4級アンモニウム塩系、スルホン酸塩系化合物、アルキルホスフェート系化合物等が挙げられる。
帯電防止剤は1種類で用いても良いし2種以上を組み合わせて用いても良い。帯電防止剤の含有量は、樹脂成分(A成分)100重量部に対し、好ましくは0.05〜5重量部、より好ましくは0.1〜5重量部である。
<Antistatic agent>
The composition of the present invention may contain an antistatic agent. Examples of the antistatic agent include (β-lauramidopropionyl) trimethylammonium sulfate, quaternary ammonium salts such as sodium dodecylbenzenesulfonate, sulfonate compounds, and alkyl phosphate compounds.
One type of antistatic agent may be used, or two or more types may be used in combination. The content of the antistatic agent is preferably 0.05 to 5 parts by weight, more preferably 0.1 to 5 parts by weight with respect to 100 parts by weight of the resin component (component A).
〈可塑剤〉
本発明の組成物は可塑剤を含有していてもよい。可塑剤として、ポリエステル系可塑剤、グリセリン系可塑剤、多価カルボン酸エステル系可塑剤、リン酸エステル系可塑剤、ポリアルキレングリコール系可塑剤、およびエポキシ系可塑剤等が挙げられる。
<Plasticizer>
The composition of the present invention may contain a plasticizer. Examples of the plasticizer include polyester plasticizers, glycerin plasticizers, polycarboxylic acid ester plasticizers, phosphate ester plasticizers, polyalkylene glycol plasticizers, and epoxy plasticizers.
ポリエステル系可塑剤として、アジピン酸、セバシン酸、テレフタル酸、イソフタル酸、ナフタレンジカルボン酸、ジフェニルジカルボン酸等の酸成分とエチレングリコール、プロピレングリコール、1,3−ブタンジオール、1,4−ブタンジオール、1,6−ヘキサンジオール、ジエチレングリコール等のジオール成分からなるポリエステルやポリカプロラクトン等のヒドロキシカルボン酸からなるポリエステル等が挙げられる。これらのポリエステルは単官能カルボン酸または単官能アルコールで末端封止されていても良い。 As a polyester plasticizer, acid components such as adipic acid, sebacic acid, terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, diphenyldicarboxylic acid and ethylene glycol, propylene glycol, 1,3-butanediol, 1,4-butanediol, Examples thereof include polyesters composed of diol components such as 1,6-hexanediol and diethylene glycol, and polyesters composed of hydroxycarboxylic acids such as polycaprolactone. These polyesters may be end-capped with a monofunctional carboxylic acid or a monofunctional alcohol.
グルセリン系可塑剤として、グリセリンモノステアレート、グリセリンジステアレート、グリセリンモノアセトモノラウレート、グリセリンモノアセトモノステアレート、グリセリンジアセトモノオレート、グリセリンモノアセトモノモンタネート等が挙げられる。 Examples of the glycerol plasticizer include glycerol monostearate, glycerol distearate, glycerol monoacetomonolaurate, glycerol monoacetomonostearate, glycerol diacetomonooleate, and glycerol monoacetomonomontanate.
多価カルボン酸系可塑剤として、フタル酸ジメチル、フタル酸ジエチル、フタル酸ジブチル、フタル酸ジヘプチル、フタル酸ジベンジル、フタル酸ブチルベンジル等のフタル酸エステル、トリメリット酸トリブチル、トリメリット酸トリオクチル、トリメリット酸トリヘキシル等のトリメリット酸エステル、アジピン酸イソデシル、アジピン酸−n−デシル−n−オクチル等のアジピン酸エステル、アセチルクエン酸トリブチル等のクエン酸エステル、アゼライン酸ビス(2−エチルヘキシル)等のアゼライン酸エステル、セバシン酸ジブチル、セバシン酸ビス(2−エチルヘキシル)等のセバシン酸エステルが挙げられる。 Polyvalent carboxylic acid plasticizers include dimethyl phthalate, diethyl phthalate, dibutyl phthalate, diheptyl phthalate, dibenzyl phthalate, butyl benzyl phthalate, trimellitic acid tributyl, trimellitic acid trioctyl, Trimellitic acid esters such as trihexyl meritate, isodecyl adipate, adipic acid esters such as adipate-n-decyl-n-octyl, citrate esters such as tributyl acetylcitrate, and bis (2-ethylhexyl) azelate Examples include sebacic acid esters such as azelaic acid ester, dibutyl sebacate, and bis (2-ethylhexyl) sebacate.
リン酸エステル系可塑剤として、リン酸トリブチル、リン酸トリス(2−エチルヘキシル)、リン酸トリオクチル、リン酸トリフェニル、リン酸トリクレジル、リン酸ジフェニル−2−エチルヘキシル等が挙げられる。 Examples of the phosphate ester plasticizer include tributyl phosphate, tris phosphate (2-ethylhexyl), trioctyl phosphate, triphenyl phosphate, tricresyl phosphate, diphenyl-2-ethylhexyl phosphate, and the like.
ポリアルキレングリコール系可塑剤として、ポリエチレングリコール、ポリプロピレングリコール、ポリテトラメチレングリコール、ポリ(エチレンオキシド.プロピレンオキシド)ブロックおよびまたはランダム共重合体、ビスフェノール類のエチレンオキシド付加重合体、ビスフェノール類のテトラヒドロフラン付加重合体等のポリアルキレングリコールあるいはその末端エポキシ変性化合物、末端エステル変性化合物および末端エーテル変性化合物等の末端封止剤化合物等が挙げられる。 Polyalkylene glycol plasticizers such as polyethylene glycol, polypropylene glycol, polytetramethylene glycol, poly (ethylene oxide.propylene oxide) block and / or random copolymers, ethylene oxide addition polymers of bisphenols, tetrahydrofuran addition polymers of bisphenols, etc. And end-capping compounds such as a terminal epoxy-modified compound, a terminal ester-modified compound, and a terminal ether-modified compound.
エポキシ系可塑剤として、エポキシステアリン酸アルキルと大豆油とからなるエポキシトリグリセリド、およびビスフェノールAとエピクロルヒドリンを原料とするエポキシ樹脂が挙げられる。 Examples of the epoxy plasticizer include an epoxy triglyceride composed of alkyl epoxy stearate and soybean oil, and an epoxy resin using bisphenol A and epichlorohydrin as raw materials.
その他の可塑剤の具体的な例としては、ネオペンチルグリコールジベンゾエート、ジエチレングリコールジベンゾエート、トリエチレングリコール−ビス(2−エチルブチレート)等の脂肪族ポリオールの安息香酸エステル、ステアリン酸アミド等の脂肪酸アミド、オレイン酸ブチル等の脂肪酸エステル、アセチルリシノール酸メチル、アセチルリシノール酸ブチル等のオキシ酸エステル、ペンタエリスリトール、各種ソルビトール、ポリアクリル酸エステル、シリコーンオイル、およびパラフィン類等が挙げられる。 Specific examples of other plasticizers include benzoic acid esters of aliphatic polyols such as neopentyl glycol dibenzoate, diethylene glycol dibenzoate, triethylene glycol-bis (2-ethylbutyrate), and fatty acids such as stearamide. Examples thereof include fatty acid esters such as amide and butyl oleate, oxyacid esters such as methyl acetylricinoleate and butyl acetylricinoleate, pentaerythritol, various sorbitols, polyacrylic acid esters, silicone oils, and paraffins.
可塑剤として、特にポリエステル系可塑剤およびポリアルキレン系可塑剤から選択された少なくとも1種よりなるものが好ましく使用でき、1種のみでも良くまた2種以上を併用することもできる。 As the plasticizer, at least one selected from polyester-type plasticizers and polyalkylene-type plasticizers can be preferably used, and only one type may be used or two or more types may be used in combination.
可塑剤の含有量は、樹脂成分(A成分)100重量部当たり、好ましくは0.01〜30重量部、より好ましくは0.05〜20重量部、さらに好ましくは0.1〜10重量部である。本発明においては結晶化核剤と可塑剤を各々単独で使用してもよいし、両者を併用して使用することがさらに好ましい。 The content of the plasticizer is preferably 0.01 to 30 parts by weight, more preferably 0.05 to 20 parts by weight, still more preferably 0.1 to 10 parts by weight per 100 parts by weight of the resin component (component A). is there. In the present invention, each of the crystallization nucleating agent and the plasticizer may be used alone, or more preferably used in combination.
〈滴下防止剤〉
本発明の組成物には、J成分として滴下防止剤を含むことができる。滴下防止剤としては、フィブリル形成能を有する含フッ素ポリマーとポリフェニレンエーテルから選ばれる少なくとも1種である。
<Anti-dripping agent>
The composition of the present invention may contain an anti-dripping agent as the J component. The anti-dripping agent is at least one selected from a fluorine-containing polymer having a fibril-forming ability and polyphenylene ether.
(フィブリル形成能を有する含フッ素ポリマー)
フィブリル形成能を有する含フッ素ポリマーとしてはポリテトラフルオロエチレン、テトラフルオロエチレン系共重合体(例えば、テトラフルオロエチレン/ヘキサフルオロプロピレン共重合体、など)、米国特許第4379910号公報に示されるような部分フッ素化ポリマー、フッ素化ジフェノールから製造されるポリカーボネート樹脂などを挙げることかできるが、好ましくはポリテトラフルオロエチレン(以下PTFEと称することがある)である。
(Fluoropolymer with fibril-forming ability)
Examples of the fluorinated polymer having fibril-forming ability include polytetrafluoroethylene, tetrafluoroethylene copolymers (for example, tetrafluoroethylene / hexafluoropropylene copolymers, etc.), as shown in US Pat. No. 4,379,910. Examples thereof include a partially fluorinated polymer and a polycarbonate resin produced from a fluorinated diphenol. Polytetrafluoroethylene (hereinafter sometimes referred to as PTFE) is preferred.
フィブリル形成能を有するポリテトラフルオロエチレン(フィブリル化PTFE)は極めて高い分子量を有し、せん断力などの外的作用によりPTFE同士を結合して繊維状になる傾向を示すものである。その数平均分子量は、150万〜数千万の範囲である。かかる下限はより好ましくは300万である。かかる数平均分子量は、特開平6−145520号公報に開示されているとおり、380℃でのポリテトラフルオロエチレンの溶融粘度に基づき算出される。即ち、フィブリル化PTFEは、かかる公報に記載された方法で測定される380℃における溶融粘度が107〜1013poiseの範囲であり、好ましくは108〜1012poiseの範囲である。 Polytetrafluoroethylene (fibrillated PTFE) having a fibril-forming ability has a very high molecular weight, and tends to form a fiber by bonding PTFE to each other by an external action such as shearing force. Its number average molecular weight ranges from 1.5 million to tens of millions. The lower limit is more preferably 3 million. The number average molecular weight is calculated based on the melt viscosity of polytetrafluoroethylene at 380 ° C. as disclosed in JP-A-6-145520. That is, fibrillated PTFE has a melt viscosity at 380 ° C. measured by the method described in this publication in the range of 107 to 1013 poise, preferably in the range of 108 to 1012 poise.
かかるPTFEは、固体形状の他、水性分散液形態のものも使用可能である。またかかるフィブリル形成能を有するPTFEは樹脂中での分散性を向上させ、更に良好な難燃性および機械的特性を得るために他の樹脂との混合形態のPTFE混合物を使用することも可能である。また、特開平6−145520号公報に開示されているとおり、かかるフィブリル化PTFEを芯とし、低分子量のポリテトラフルオロエチレンを殻とした構造を有するものも好ましく利用される。 Such PTFE can be used in solid form or in the form of an aqueous dispersion. In addition, PTFE having such fibril-forming ability can improve the dispersibility in the resin, and it is also possible to use a PTFE mixture in a mixed form with other resins in order to obtain better flame retardancy and mechanical properties. is there. Further, as disclosed in JP-A-6-145520, those having a structure having such a fibrillated PTFE as a core and a low molecular weight polytetrafluoroethylene as a shell are also preferably used.
フィブリル化PTFEの市販品としては例えば三井・デュポンフロロケミカル(株)のテフロン(登録商標)6J、ダイキン化学工業(株)のポリフロンMPA FA500、F−201Lなどを挙げることができる。フィブリル化PTFEの水性分散液の市販品としては、旭アイシーアイフロロポリマーズ(株)製のフルオンAD−1、AD−936、ダイキン工業(株)製のフルオンD−1、D−2、三井・デュポンフロロケミカル(株)製のテフロン(登録商標)30Jなどを代表として挙げることができる。 Examples of commercially available fibrillated PTFE include Teflon (registered trademark) 6J from Mitsui DuPont Fluorochemical Co., Ltd., Polyflon MPA FA500, F-201L from Daikin Chemical Industries, Ltd., and the like. Commercially available aqueous dispersions of fibrillated PTFE include: Fluon AD-1, AD-936 manufactured by Asahi IC Fluoropolymers, Fluon D-1, D-2 manufactured by Daikin Industries, Ltd., Mitsui A representative example is Teflon (registered trademark) 30J manufactured by DuPont Fluorochemical Co., Ltd.
混合形態のフィブリル化PTFEとしては、(1)フィブリル化PTFEの水性分散液と有機重合体の水性分散液または溶液とを混合し共沈殿を行い共凝集混合物を得る方法(特開昭60−258263号公報、特開昭63−154744号公報などに記載された方法)、(2)フィブリル化PTFEの水性分散液と乾燥した有機重合体粒子とを混合する方法(特開平4−272957号公報に記載された方法)、(3)フィブリル化PTFEの水性分散液と有機重合体粒子溶液を均一に混合し、かかる混合物からそれぞれの媒体を同時に除去する方法(特開平06−220210号公報、特開平08−188653号公報などに記載された方法)、(4)フィブリル化PTFEの水性分散液中で有機重合体を形成する単量体を重合する方法(特開平9−95583号公報に記載された方法)、および(5)PTFEの水性分散液と有機重合体分散液を均一に混合後、更に該混合分散液中でビニル系単量体を重合し、その後混合物を得る方法(特開平11−29679号などに記載された方法)により得られたものが使用できる。これらの混合形態のフィブリル化PTFEの市販品としては、三菱レイヨン(株)の「メタブレン A3800」(商品名)、GEスペシャリティーケミカルズ社製 「BLENDEX B449」(商品名)およびPacific Interchem Corporation社製「POLY TS AD001」(商品名)などが例示される。混合形態におけるフィブリル化PTFEの割合としては、かかる混合物100重量%中、フィブリル化PTFEが10〜80重量%が好ましく、より好ましくは15〜75重量%である。フィブリル化PTFEの割合がかかる範囲にある場合は、フィブリル化PTFEの良好な分散性を達成することができる。 As a mixed form of fibrillated PTFE, (1) a method in which an aqueous dispersion of fibrillated PTFE and an aqueous dispersion or solution of an organic polymer are mixed and co-precipitated to obtain a co-agglomerated mixture (JP-A-60-258263). (2) A method of mixing an aqueous dispersion of fibrillated PTFE and dried organic polymer particles (Japanese Patent Laid-Open No. 4-272957). Described method), (3) A method in which an aqueous dispersion of fibrillated PTFE and an organic polymer particle solution are uniformly mixed, and the respective media are simultaneously removed from the mixture (Japanese Patent Laid-Open Nos. 06-220210, (Method described in Japanese Patent Application Laid-Open No. 08-188653), (4) A method of polymerizing monomers forming an organic polymer in an aqueous dispersion of fibrillated PTFE (Method described in JP-A-9-95583), and (5) an aqueous dispersion of PTFE and an organic polymer dispersion are uniformly mixed, and then a vinyl monomer is further polymerized in the mixed dispersion. Thereafter, those obtained by a method for obtaining a mixture (a method described in JP-A No. 11-29679) can be used. Commercial products of these mixed forms of fibrillated PTFE include “Metablene A3800” (trade name) manufactured by Mitsubishi Rayon Co., Ltd., “BLENDEX B449” (trade name) manufactured by GE Specialty Chemicals, and “Products manufactured by Pacific Interchem Corporation” “POLY TS AD001” (product name) is exemplified. The proportion of fibrillated PTFE in the mixed form is preferably 10 to 80% by weight, more preferably 15 to 75% by weight, in 100% by weight of the mixture. When the ratio of fibrillated PTFE is in such a range, good dispersibility of fibrillated PTFE can be achieved.
フィブリル形成能を有する含フッ素ポリマーの含有量は、樹脂成分(A成分)100重量部を基準として、0.01〜3重量部が好ましく、より好ましくは0.01〜2重量部、さらに好ましくは0.05〜1.5重量部である。 The content of the fluoropolymer having fibril-forming ability is preferably 0.01 to 3 parts by weight, more preferably 0.01 to 2 parts by weight, and still more preferably based on 100 parts by weight of the resin component (component A). 0.05 to 1.5 parts by weight.
(ポリフェニレンエーテル)
ポリフェニレンエーテルとは、フェニレンエーテル構造を有するフェノールの重合体または共重合体(以下単にPPE重合体と略称する場合がある)である。
PPE重合体の具体例としては、ポリ(オキシ−1,4−フェニレン)、ポリ(オキシ−2,6−ジメチルフェニレン−1,4−ジイル)、ポリ(オキシ−2−メチル−6−エチルフェニレン−1,4−ジイル)、ポリ(オキシ−2,6−ジエチルフェニレン−1,4−ジイル)、ポリ(オキシ−2−エチル−6−n−プロピルフェニレン−1,4−ジイル)、ポリ(オキシ−2,6−ジ(n−プロピル)フェニレン−1,4−ジイル)、ポリ(オキシ−2−メチル−6−n−ブチルフェニレン−1,4−ジイル)、ポリ(オキシ−2−エチル−6−イソプロピルフェニレン−1,4−ジイル)、ポリ(オキシ−2−メチル−6−ヒドロキシエチルフェニレン−1,4−ジイル)、ポリ(オキシ−2−メチル−6−クロロエチルフェニレン−1,4−ジイル)等が挙げられる。この中で、ポリ(オキシ−2,6−ジメチルフェニレン−1,4−ジイル)が特に好ましい。
(Polyphenylene ether)
The polyphenylene ether is a phenol polymer or copolymer having a phenylene ether structure (hereinafter sometimes simply referred to as a PPE polymer).
Specific examples of PPE polymers include poly (oxy-1,4-phenylene), poly (oxy-2,6-dimethylphenylene-1,4-diyl), and poly (oxy-2-methyl-6-ethylphenylene). -1,4-diyl), poly (oxy-2,6-diethylphenylene-1,4-diyl), poly (oxy-2-ethyl-6-n-propylphenylene-1,4-diyl), poly ( Oxy-2,6-di (n-propyl) phenylene-1,4-diyl), poly (oxy-2-methyl-6-n-butylphenylene-1,4-diyl), poly (oxy-2-ethyl) -6-isopropylphenylene-1,4-diyl), poly (oxy-2-methyl-6-hydroxyethylphenylene-1,4-diyl), poly (oxy-2-methyl-6-chloroethylphenylene) , 4-diyl), and the like. Of these, poly (oxy-2,6-dimethylphenylene-1,4-diyl) is particularly preferred.
フェニレンエーテル構造を有する共重合体としては、2,6−ジメチルフェノールと2,3,6−トリメチルフェノールとの共重合体、2,6−ジメチルフェノールとo−クレゾールとの共重合体あるいは2,6−ジメチルフェノールと2,3,6−トリメチルフェノールおよびo−クレゾールとの共重合体等が例示される。 Examples of the copolymer having a phenylene ether structure include a copolymer of 2,6-dimethylphenol and 2,3,6-trimethylphenol, a copolymer of 2,6-dimethylphenol and o-cresol, or 2, Examples include a copolymer of 6-dimethylphenol, 2,3,6-trimethylphenol and o-cresol.
上記のPPE重合体の製造方法は特に限定されるものではなく、例えば米国特許4788277号明細書に記載されている方法等に従って、酸化カップリング重合により製造することができる。 The method for producing the PPE polymer is not particularly limited, and can be produced by oxidative coupling polymerization according to, for example, the method described in US Pat. No. 4,788,277.
また、ポリフェニレンエーテルの分子量は、例えば分子量パラメーターとして、(0.5g/dlクロロホルム溶液、30℃)還元粘度が0.05〜0.70dl/gの範囲が好ましく、0.10〜0.55dl/gの範囲がより好ましい。
また、ポリフェニレンエーテル中には、本発明の主旨に反しない限り、種々のフェニレンエーテルユニットを部分構造として含んでいても構わない。
The molecular weight of polyphenylene ether is, for example, preferably as a molecular weight parameter (0.5 g / dl chloroform solution, 30 ° C.), with a reduced viscosity in the range of 0.05 to 0.70 dl / g, preferably 0.10 to 0.55 dl / g. The range of g is more preferable.
Further, the polyphenylene ether may contain various phenylene ether units as partial structures as long as it does not contradict the gist of the present invention.
かかる構造としては、例えば特開昭63−12698号公報、特開昭63−301222号公報などに記載されている、オキシ−2−(N、N−ジアルキルアミノメチル)−6−メチルフェニレン−1,4−ジイルユニットやオキシ−2−(N−アルキル−N−フェニルアミノメチル)−6−メチルフェニレン−1,4−ジイルユニット等が挙げられる。また、ポリフェニレンエーテルの主鎖中にジフェノキノン等が少量結合したものも含まれる。 As such a structure, for example, oxy-2- (N, N-dialkylaminomethyl) -6-methylphenylene-1 described in JP-A Nos. 63-12698 and 63-301222 is disclosed. , 4-diyl unit, oxy-2- (N-alkyl-N-phenylaminomethyl) -6-methylphenylene-1,4-diyl unit, and the like. Also included are those in which a small amount of diphenoquinone or the like is bonded to the main chain of polyphenylene ether.
PPE重合体には、下記のα,β−不飽和カルボン酸またはその無水物等のエチレン性不飽和化合物により変性されたポリフェニレンエーテルも含むことができる。かかる変性ポリフェニレンエーテルを用いた場合には、ビニル化合物重合体との混合性に優れ、相剥離等のない成形体を提供できる。 The PPE polymer may also contain polyphenylene ether modified with an ethylenically unsaturated compound such as the following α, β-unsaturated carboxylic acid or anhydride thereof. When such a modified polyphenylene ether is used, it is possible to provide a molded article having excellent mixing properties with a vinyl compound polymer and free from phase separation.
α,β−不飽和カルボン酸またはその無水物の例として、特公昭49−2343号公報、特公平3−52486号公報等に記載される無水マレイン酸、フタル酸、無水イタコン酸、無水グルタコン酸、無水シトラコン酸、無水アコニット酸、無水ハイミツク酸、5−ノルボルネン−2−メチル−2−カルボン酸、あるいはマレイン酸、フマル酸等が挙げられ、これらに限定されるものではないが、無水マレイン酸が特に好ましい。 Examples of α, β-unsaturated carboxylic acids or anhydrides thereof include maleic anhydride, phthalic acid, itaconic anhydride, and glutaconic anhydride described in JP-B-49-2343 and JP-B-3-52486. Citraconic anhydride, aconitic anhydride, hymic anhydride, 5-norbornene-2-methyl-2-carboxylic acid, or maleic acid, fumaric acid, etc., but are not limited thereto, maleic anhydride Is particularly preferred.
PPEは上記エチレン性不飽和化合物により、有機過酸化物の存在下、または非存在下、PPEのガラス転移温度以上の温度まで加熱することによって変性することができる。 PPE can be modified with the ethylenically unsaturated compound by heating to a temperature equal to or higher than the glass transition temperature of PPE in the presence or absence of an organic peroxide.
本発明において、あらかじめ上記エチレン性不飽和化合物により変成されたPPE樹脂を用いてもよい。また、本発明組成物を製造する際に同時に、上記エチレン性不飽和化合物を添加することによりポリフェニレンエーテル重合体と反応させることもできる。 In the present invention, a PPE resin previously modified with the ethylenically unsaturated compound may be used. Moreover, it can also be made to react with a polyphenylene ether polymer by adding the said ethylenically unsaturated compound simultaneously when manufacturing this invention composition.
ポリフェニレンエーテルの含有量は、樹脂成分(A成分)100重量部当り、好ましくは0.1〜30重量部、より好ましくは0.5〜25重量部、さらに好ましくは1〜20重量部である。
なお、使用、目的に応じて、前記フィブリル形成能を有する含フッ素ポリマーとポリフェニレンエーテルを組み合わせて使用してもよい。
The content of polyphenylene ether is preferably 0.1 to 30 parts by weight, more preferably 0.5 to 25 parts by weight, and still more preferably 1 to 20 parts by weight per 100 parts by weight of the resin component (component A).
In addition, according to use and the objective, you may use combining the fluorine-containing polymer which has the said fibril formation ability, and polyphenylene ether.
〈その他〉
また本発明においては、本発明の趣旨に反しない範囲において、フェノール樹脂、メラミン樹脂、熱硬化性ポリエステル樹脂、シリコーン樹脂、エポキシ樹脂等の熱硬化性樹脂を含有させても良い。また有機、無機系の染料、顔料を含む着色剤、例えば、二酸化チタン等の酸化物、アルミナホワイト等の水酸化物、硫化亜鉛等の硫化物、紺青等のフェロシアン化物、ジンククロメート等のクロム酸塩、硫酸バリウム等の硫酸塩、炭酸カルシウム等の炭酸塩、群青等の珪酸塩、マンガンバイオレット等のリン酸塩、カーボンブラック等の炭素、ブロンズ粉やアルミニウム粉等の金属着色剤等を含有させても良い。また、ナフトールグリーンB等のニトロソ系、ナフトールイエローS等のニトロ系、ナフトールレッド、クロモフタルイエローどのアゾ系、フタロシアニンブルーやファストスカイブルー等のフタロシアニン系、インダントロンブルー等の縮合多環系着色剤等、グラファイト、フッソ樹脂等の摺動性改良剤等の添加剤を含有させても良い。これらの添加剤は単独であるいは2種以上を併用することもできる。
<Others>
Moreover, in this invention, you may contain thermosetting resins, such as a phenol resin, a melamine resin, a thermosetting polyester resin, a silicone resin, an epoxy resin, in the range which is not contrary to the meaning of this invention. Colorants containing organic and inorganic dyes and pigments, for example, oxides such as titanium dioxide, hydroxides such as alumina white, sulfides such as zinc sulfide, ferrocyanides such as bitumen, and chromium such as zinc chromate Contains acid salts, sulfates such as barium sulfate, carbonates such as calcium carbonate, silicates such as ultramarine, phosphates such as manganese violet, carbon such as carbon black, metal colorants such as bronze powder and aluminum powder, etc. You may let them. Also, nitroso type such as naphthol green B, nitro type such as naphthol yellow S, azo type such as naphthol red, chromophthal yellow, phthalocyanine type such as phthalocyanine blue and fast sky blue, and condensed polycyclic colorants such as indanthrone blue In addition, additives such as slidability improvers such as graphite and fluorine resin may be added. These additives can be used alone or in combination of two or more.
〈組成物の製造方法〉
本発明の組成物は、(i) 100重量部のポリ−L乳酸(A−1成分)に対して、0.001〜3重量部のホスホノ脂肪酸エステル(B成分)を含有する組成物−1および100重量部のポリ−D乳酸(A−2成分)に対して、0.001〜3重量部のホスホノ脂肪酸エステル(B成分)を含有する組成物−2を、組成物−1および組成物−2の合計100重量部に対して、0.01〜5重量部のリン酸エステル金属塩(C成分)の存在下、溶融混練してステレオコンプレックスポリ乳酸を調製する工程、並びに
(ii) 得られたステレオコンプレックスポリ乳酸5〜95wt%と芳香族ポリカーボネート(A−β成分)95〜5wt%からなる樹脂成分100重量部に対し、0.001〜2重量部のホスホノ脂肪酸エステル(B成分)、0.001〜2重量部の、ホスファイト系化合物、ホスホナイト系化合物、ヒンダートフェノール系化合物、チオエーテル系化合物からなる群より選ばれる少なくとも一種の酸化防止剤(D成分)、並びに0.001〜10重量部の末端封鎖剤(E成分)を溶融混練する工程、
により製造することができる。
<Method for producing composition>
The composition of the present invention is (i) a composition-1 containing 0.001 to 3 parts by weight of a phosphono fatty acid ester (component B) with respect to 100 parts by weight of poly-L lactic acid (component A-1). And Composition-2 containing 0.001 to 3 parts by weight of phosphono fatty acid ester (B component) to 100 parts by weight of poly-D lactic acid (A-2 component) -2 for a total of 100 parts by weight to prepare stereocomplex polylactic acid by melt-kneading in the presence of 0.01 to 5 parts by weight of a phosphoric acid ester metal salt (component C), and (ii) 0.001 to 2 parts by weight of a phosphono fatty acid ester (B component) with respect to 100 parts by weight of the resin component consisting of 5 to 95 wt% of the obtained stereocomplex polylactic acid and 95 to 5 wt% of an aromatic polycarbonate (A-β component), 0 0.001 to 2 parts by weight of at least one antioxidant (component D) selected from the group consisting of phosphite compounds, phosphonite compounds, hindered phenol compounds, and thioether compounds, and 0.001 to 10 weights A step of melt-kneading a part of the end-capping agent (E component),
Can be manufactured.
本発明の製造方法の特徴は、ポリ−L乳酸(A−1成分)、ポリ−D乳酸(A−2成分)の重合終了時に、ポリ乳酸の金属重合触媒の失活剤としてホスホノ脂肪酸エステル(B成分)を添加し、その後、酸化防止剤(D成分)と溶融混練する際にもホスホノ脂肪酸エステル(B成分)を添加することにある。組成物を調製する最終段階にもホスホノ脂肪酸エステル(B成分)を添加することにより、揮発し易いホスホノ脂肪酸エステル(B成分)を、残留する金属重合触媒と常に共存させることが出来、触媒の失活効果を維持することが出来る。その結果、熱安定性に優れたポリ乳酸組成物を得ることができる。 The production method of the present invention is characterized by a phosphono fatty acid ester (as a deactivator of a metal polymerization catalyst of polylactic acid at the end of polymerization of poly-L lactic acid (A-1 component) and poly-D lactic acid (A-2 component). (B component) is added, and then phosphono fatty acid ester (B component) is also added when melt-kneading with an antioxidant (D component). By adding the phosphono fatty acid ester (component B) to the final stage of preparing the composition, the easily volatile phosphono fatty acid ester (component B) can always coexist with the remaining metal polymerization catalyst. The live effect can be maintained. As a result, a polylactic acid composition excellent in thermal stability can be obtained.
工程(i)において、組成物−1は、100重量部のポリ−L乳酸(A−1成分)に対して、好ましくは0.005〜2重量部、より好ましくは0.01〜1重量部のホスホノ脂肪酸エステル(B成分)を含有する。組成物−2は、100重量部のポリ−L乳酸(A−1成分)に対して、好ましくは0.05〜2重量部、より好ましくは0.01〜1重量部のホスホノ脂肪酸エステル(B成分)を含有する。 In step (i), composition-1 is preferably 0.005 to 2 parts by weight, more preferably 0.01 to 1 part by weight, based on 100 parts by weight of poly-L lactic acid (component A-1). Phosphono fatty acid ester (component B). Composition-2 is preferably 0.05 to 2 parts by weight, more preferably 0.01 to 1 part by weight of phosphono fatty acid ester (B) with respect to 100 parts by weight of poly-L lactic acid (component A-1). Component).
工程(ii)において、ホスホノ脂肪酸エステル(B成分)の添加量は、ステレオコンプレックスポリ乳酸5〜95wt%とメタクリル系樹脂(A−β成分)95〜5wt%からなる樹脂成分100重量部に対して、好ましくは0.005〜2重量部、より好ましくは0.01〜1重量部である。また酸化防止剤(D成分)の添加量は、100重量部のステレオコンプレックスポリ乳酸に対して、好ましくは0.005〜1.5重量部、より好ましくは0.01〜1重量部である。 In step (ii), the amount of phosphono fatty acid ester (component B) added is 100 parts by weight of a resin component consisting of stereocomplex polylactic acid 5 to 95 wt% and methacrylic resin (A-β component) 95 to 5 wt%. The amount is preferably 0.005 to 2 parts by weight, more preferably 0.01 to 1 part by weight. The addition amount of the antioxidant (component D) is preferably 0.005 to 1.5 parts by weight, more preferably 0.01 to 1 part by weight with respect to 100 parts by weight of the stereocomplex polylactic acid.
ステレオコンプレックスポリ乳酸を製造する工程の溶融混練として、溶融温度は好ましくは250〜300℃、より好ましくは250〜290℃である。300℃を超えると、分解反応を抑制するのが難しくなるので好ましくなく、240℃未満の温度では熱処理による均一混合が進まず、ステレオコンプレックスが効率的に生成し難くなるので好ましくない。溶融時間は特に限定されるものではないが、0.2〜60分、好ましくは1〜20分である。溶融時の雰囲気は、常圧の不活性雰囲気下、または減圧のいずれも適用可能である。 As melt kneading in the step of producing stereocomplex polylactic acid, the melting temperature is preferably 250 to 300 ° C, more preferably 250 to 290 ° C. If it exceeds 300 ° C., it is not preferable because it becomes difficult to suppress the decomposition reaction, and if it is less than 240 ° C., uniform mixing by heat treatment does not proceed, and it is difficult to efficiently produce a stereocomplex. The melting time is not particularly limited, but is 0.2 to 60 minutes, preferably 1 to 20 minutes. As the atmosphere at the time of melting, either an inert atmosphere at normal pressure or a reduced pressure is applicable.
溶融混練には、タンブラー、V型ブレンダー、スーパーミキサー、ナウターミキサー、バンバリーミキサー、混練ロール、1軸または2軸の押出機等を用いることができる。得られる組成物は、そのままで、または溶融押出機で一旦ペレット状にしてから、成形することができる。 For melt kneading, a tumbler, V-type blender, super mixer, nauter mixer, Banbury mixer, kneading roll, uniaxial or biaxial extruder, or the like can be used. The resulting composition can be molded as it is or after being once pelletized with a melt extruder.
本発明のポリ乳酸組成物は、ペレット状であることが好ましい。ペレットはストランド、あるいは板状におしだされたポリ乳酸組成物を、樹脂が完全に固化した後、あるいは完全には固化されないで、いまだ溶融状態にあるとき、空気中、あるいは水中でカッティングする等の手法が従来公知であるが、本発明においてはいずれも好適に適用できる。 The polylactic acid composition of the present invention is preferably in the form of pellets. The pellets are cut into strands or plate-like polylactic acid compositions in the air or water after the resin is completely solidified or not completely solidified and still in the molten state Such methods are conventionally known, but any of them can be suitably applied in the present invention.
ペレットの形状は、たとえば、眞球状、ダイス状、直線状、曲線状、断面面の形状は、丸、楕円、扁平、三角、四角以上の多角形および星形などいずれの形状であっても良いが、ペレットをさらに各種成形方法で成形するに好適な形状を有するのが好ましい。具体的にはペレット長は1〜7mm、長径3〜5mm、短径1〜4mmのものが好ましい。またかかる形状はばらつきのないものが好ましい。 The shape of the pellet may be any shape such as a spherical shape, a die shape, a linear shape, a curved shape, and a cross-sectional shape such as a circle, an ellipse, a flat shape, a triangle, a polygon having a square shape or more, and a star shape. However, it is preferable to have a shape suitable for further molding the pellets by various molding methods. Specifically, the pellet length is preferably 1 to 7 mm, the major axis is 3 to 5 mm, and the minor axis is 1 to 4 mm. Further, it is preferable that the shape does not vary.
〈組成物の物性〉
本発明の組成物の引張強度保持率(T)は、60%以上、好ましくは70%以上、より好ましくは80%以上、さらに好ましくは90%〜100%である。引張強度保持率(T)は、下記式
T(%)=t1/t0×100(%)
で表される。
但し、t0は初期引張強度、t1は80℃、95%RH雰囲気下、100時間後の引張強度である。引張強度測定用試験片は特に限定するものではないが、ISO527に準拠した長さ150mm×幅20mm×厚み4mmの試験片が好適に例示できる。引張強度試験条件は特に限定するものではないが、5mm/minの試験速度が好適に例示できる。また、引張強度としては降伏強度と破断強度が挙げられるが、本発明の引張強度とはそのいずれかの高強度の方を指し、所謂、引張試験中で測定された最大の引張強度を言う。
本発明の組成物の13C−NMRで求めたエナンチオマー平均連鎖長は、好ましくは10〜40、より好ましくは15〜40、更に好ましくは18〜39である。
<Physical properties of the composition>
The tensile strength retention (T) of the composition of the present invention is 60% or more, preferably 70% or more, more preferably 80% or more, and further preferably 90% to 100%. Tensile strength retention (T) is expressed by the following formula: T (%) = t 1 / t 0 × 100 (%)
It is represented by
However, t 0 is the initial tensile strength, and t 1 is the tensile strength after 100 hours in an atmosphere of 80 ° C. and 95% RH. Although the test piece for measuring the tensile strength is not particularly limited, a test piece having a length of 150 mm, a width of 20 mm, and a thickness of 4 mm conforming to ISO527 can be suitably exemplified. The tensile strength test conditions are not particularly limited, but a test speed of 5 mm / min can be suitably exemplified. In addition, examples of the tensile strength include yield strength and breaking strength. The tensile strength of the present invention indicates one of the higher strengths, that is, the maximum tensile strength measured in a so-called tensile test.
The enantiomeric average chain length determined by 13 C-NMR of the composition of the present invention is preferably 10 to 40, more preferably 15 to 40, and still more preferably 18 to 39.
〈成形品〉
本発明の組成物よりなる成形品は、射出成形、押出成形、熱成形、ブロー成形または発泡成形により成形したものが好ましい。
射出成形品は、従来公知の成形法が何ら限定なく適用できるが、射出成形時、成形品の結晶化、成形サイクルを上げる観点から、金型温度は好ましくは30℃以上、より好ましくは40℃以上、さらに好ましくは50℃以上である。しかし、成形品の変形を防ぐ意味において、金型温度は、好ましくは140℃以下、より好ましくは120℃以下、さらに好ましくは110℃以下である。またこれらの成形品として、自動車部品、電気・電子部品、電気機器外装部品、OA外装部品等を挙げることができる。
<Molding>
The molded product made of the composition of the present invention is preferably molded by injection molding, extrusion molding, thermoforming, blow molding or foam molding.
Conventionally known molding methods can be applied to the injection molded product without any limitation. From the viewpoint of increasing the crystallization of the molded product and the molding cycle during the injection molding, the mold temperature is preferably 30 ° C. or higher, more preferably 40 ° C. As mentioned above, More preferably, it is 50 degreeC or more. However, in order to prevent deformation of the molded product, the mold temperature is preferably 140 ° C. or lower, more preferably 120 ° C. or lower, and further preferably 110 ° C. or lower. Examples of these molded products include automobile parts, electrical / electronic parts, electrical equipment exterior parts, OA exterior parts, and the like.
以下、実施例により本発明を詳述する。ただし、本発明はこれらに限定されるものではない。 Hereinafter, the present invention will be described in detail by way of examples. However, the present invention is not limited to these.
1.ポリ乳酸の製造
下記の製造例に示す方法により、ポリ乳酸の製造を行った。また製造例中における各値は下記の方法で求めた。
1. Production of polylactic acid Polylactic acid was produced by the method shown in the production examples below. Moreover, each value in a manufacture example was calculated | required with the following method.
(1)ポリマーの重量平均分子量(Mw)および数平均分子量(Mn):
ゲルパーミエーションクロマトグラフィー(GPC)により測定、標準ポリスチレンに換算した。GPC測定機器は、検出器として、示差屈折計島津RID−6Aを用い、カラムとして東ソ−TSKgelG3000HXLを使用した。測定は、クロロホルムを溶離液とし温度40℃、流速1.0ml/minにて、濃度1mg/ml(1%ヘキサフルオロイソプロパノールを含むクロロホルム)の試料を10μl注入することにより行った。
(1) Weight average molecular weight (Mw) and number average molecular weight (Mn) of the polymer:
It was measured by gel permeation chromatography (GPC) and converted to standard polystyrene. The GPC measurement instrument used a differential refractometer Shimadzu RID-6A as a detector and Toso-TSKgel G3000HXL as a column. The measurement was performed by injecting 10 μl of a sample having a concentration of 1 mg / ml (chloroform containing 1% hexafluoroisopropanol) at a temperature of 40 ° C. and a flow rate of 1.0 ml / min using chloroform as an eluent.
(2)カルボキシル基濃度
試料を精製o−クレゾールに窒素気流下で溶解した後、ブロモクレゾールブルーを指示薬とし、0.05規定水酸化カリウムのエタノール溶液で滴定した。
(2) Carboxyl group concentration The sample was dissolved in purified o-cresol under a nitrogen stream, and then titrated with 0.05 N potassium hydroxide in ethanol using bromocresol blue as an indicator.
(3)示差走査熱量計(DSC)の測定
DSC(TAインストルメント社製 TA−2920)を用いて試料の一回目の昇温過程において、190℃以上の融解ピークをステレオ結晶由来の融解ピークとし、その融解温度をTms、融解エンタルピーをHmsとした。また、190℃以下の融解ピークをホモ結晶由来の融解ピークとし、その融解温度をTmh、融解エンタルピーをHmhとして、下記式より、ステレオコンプレックス形成度のパラメーターを評価した。
ステレオ化度=△Hms/(△Hms+△Hmh)×100
(3) Measurement with a differential scanning calorimeter (DSC) In the first heating process of the sample using DSC (TA-2920, manufactured by TA Instrument Co., Ltd.), a melting peak at 190 ° C. or higher was used as a melting peak derived from stereo crystals. The melting temperature was Tms and the melting enthalpy was Hms. In addition, the melting peak at 190 ° C. or less was defined as a homocrystalline melting peak, the melting temperature was Tmh, and the melting enthalpy was Hmh.
Stereogenicity = ΔHms / (ΔHms + ΔHmh) × 100
(4)エナンチオマー平均連鎖長
試料をHFIP/クロロホルム=1/1混合溶媒に溶解した後、メタノールで再沈させた。この再沈ポリマー成分をメタノールで超音波洗浄し、遠心分離を10回繰り返して不純物や溶媒成分を除去した後、真空乾燥機で1日乾燥し、測定サンプルとなり得るポリ乳酸成分を抽出した。
このようにして抽出した試料を用い、エナンチオマー平均連鎖長を以下のように測定した。
13−CNMR装置:日本ブルカー製 BURKER ARX−500
サンプル:50mg/0.7ml
測定溶媒:10% HFIP含有重水素化クロロホルム
内部標準:テトラメチルシラン(TMS)1%(v/v)
測定温度:27℃(300K)
測定周波数:125MHz
13C−NMR測定により、カルボニル炭素(C=O)に帰属される炭素のピークのうち、ピーク(a)(170.1−170.3MHz辺り)はホモ配列(LLLLLLまたはDDDDDD)に、ピーク(b)(170.0−169.8MHz辺り)はラセミ鎖(LLLDDD…)に帰属し、これらのピークの積分値から、下記の式により平均連鎖長を算出した。
v=ピーク(a)の積分値/ピーク(b)の積分値
本発明の実施例、比較例においては、以下の材料を使用した。
(4) Enantiomeric average chain length The sample was dissolved in HFIP / chloroform = 1/1 mixed solvent and then reprecipitated with methanol. This reprecipitation polymer component was ultrasonically washed with methanol, and centrifugation was repeated 10 times to remove impurities and solvent components, followed by drying with a vacuum dryer for 1 day to extract a polylactic acid component that could be a measurement sample.
Using the sample thus extracted, the average enantiomeric chain length was measured as follows.
13- C NMR apparatus: BURKER ARX-500 manufactured by Nippon Bruker
Sample: 50mg / 0.7ml
Measurement solvent: 10% HFIP-containing deuterated chloroform Internal standard: Tetramethylsilane (TMS) 1% (v / v)
Measurement temperature: 27 ° C (300K)
Measurement frequency: 125 MHz
The 13 C-NMR measurement, out of carbon peaks attributed to carbonyl carbon (C = O), a peak (a) (170.1-170.3MHz around) the homo sequence (LLLLLL or DDDDDD), peaks ( b) (around 170.0-169.8 MHz) belongs to the racemic chain (LLLDDD...), and the average chain length was calculated from the integrated value of these peaks by the following formula.
v = Integral value of peak (a) / Integral value of peak (b) In the examples and comparative examples of the present invention, the following materials were used.
[参考例:ジ−n−ヘキシルホスホノ酢酸エチル(DHPA)の合成]
亜リン酸トリヘキシル100重量部とブロモ酢酸エチル100重量部とを反応容器に入れ、内部を窒素置換した。つづいて反応容器を170℃に昇温して、加熱還流させながら3時間反応を実施した。反応混合物を80℃で過剰のブロモ酢酸エチルを減圧留去した後、190℃で減圧蒸留を行い、無色透明な液体を得た(収率84%、沸点146℃/0.5mmHg)。
[Reference Example: Synthesis of ethyl di-n-hexylphosphonoacetate (DHPA)]
100 parts by weight of trihexyl phosphite and 100 parts by weight of ethyl bromoacetate were placed in a reaction vessel, and the interior was purged with nitrogen. Subsequently, the reaction vessel was heated to 170 ° C., and the reaction was carried out for 3 hours while heating to reflux. After excess ethyl bromoacetate was distilled off at 80 ° C. under reduced pressure, the reaction mixture was distilled under reduced pressure at 190 ° C. to obtain a colorless transparent liquid (yield 84%, boiling point 146 ° C./0.5 mmHg).
[A−α−1成分:ポリL−乳酸の製造(PLLA)]
[製造例1]
冷却留出管を備えた重合反応容器の原料仕込み口から、窒素気流下でL−ラクチド(株式会社武蔵野化学研究所製、光学純度100%)100重量部およびステアリルアルコール0.15重量部を仕込んだ。続いて反応容器内を5回窒素置換し、L−ラクチドを190℃にて融解させた。L−ラクチドが完全に融解した時点で、オクチル酸スズを0.005重量部のトルエン500μL溶液を添加し、190℃で1時間重合した。重合終了後、ジ−n−ヘキシルホスホノ酢酸エチル0.082重量部を原料仕込み口から添加し、15分間混練した。最後に余剰のL−ラクチドを脱揮して、反応容器内から重合物を吐出し、チップ化し、ポリ−L乳酸(PLLA)を得た。
得られたポリL−乳酸樹脂の重量平均分子量は15.1万、ガラス転移点(Tg)55℃、融解ピーク温度(Tmh)は177℃、カルボキシル基含有量は15eq/ton、エナンチオマー平均連鎖長はシンジオタクチック連結部が測定できず、算出不可であった。
[A-α-1 component: production of poly L-lactic acid (PLLA)]
[Production Example 1]
100 parts by weight of L-lactide (manufactured by Musashino Chemical Laboratory, Inc., optical purity 100%) and 0.15 part by weight of stearyl alcohol are charged from a raw material charging port of a polymerization reaction vessel equipped with a cooling distillation pipe under a nitrogen stream. It is. Subsequently, the inside of the reaction vessel was purged with nitrogen five times, and L-lactide was melted at 190 ° C. When L-lactide was completely melted, 0.005 part by weight of a toluene 500 μL solution of tin octylate was added and polymerized at 190 ° C. for 1 hour. After completion of the polymerization, 0.082 part by weight of ethyl di-n-hexylphosphonoacetate was added from the raw material charging port and kneaded for 15 minutes. Finally, excess L-lactide was devolatilized, and the polymer was discharged from the reaction vessel to form a chip to obtain poly-L lactic acid (PLLA).
The resulting poly L-lactic acid resin has a weight average molecular weight of 151,000, a glass transition point (Tg) of 55 ° C., a melting peak temperature (Tmh) of 177 ° C., a carboxyl group content of 15 eq / ton, and an enantiomer average chain length. The syndiotactic connecting part could not be measured and could not be calculated.
[A−α−2成分:ポリD−乳酸の製造(PDLA)]
[製造例2]
製造例1のL−ラクチドのかわりにD−ラクチド(株式会社武蔵野化学研究所製、光学純度100%)を使用する以外は製造例1と同様の操作を行い、ポリD−乳酸(PDLA)を得た。得られたポリD−乳酸樹脂の重量平均分子量は15.2万、ガラス転移点(Tg)55℃、融解ピーク温度(Tmh)は177℃、カルボキシル基含有量は14eq/ton、エナンチオマー平均連鎖長はシンジオタクチック連結部が測定できず、算出不可であった。であった。
[A-α-2 component: Production of poly-D-lactic acid (PDLA)]
[Production Example 2]
Poly D-lactic acid (PDLA) was prepared in the same manner as in Production Example 1 except that D-lactide (manufactured by Musashino Chemical Laboratory, Inc., optical purity 100%) was used instead of L-lactide in Production Example 1. Obtained. The resulting poly-D-lactic acid resin has a weight average molecular weight of 152,000, a glass transition point (Tg) of 55 ° C., a melting peak temperature (Tmh) of 177 ° C., a carboxyl group content of 14 eq / ton, and an enantiomer average chain length. The syndiotactic connecting part could not be measured and could not be calculated. Met.
[A−α−3−1成分:ステレオコンプレックスポリ乳酸−1の製造(scPLA−1)]
[製造例3−1]
製造例1および2で得られたPLLA,PDLAの各50重量部よりなるポリ乳酸樹脂計100重量部並びに燐酸−2,2’−メチレンビス(4,6−ジ−tert−ブチルフェニル)ナトリウム(アデカスタブNA−11:(株)ADEKA製)0.1重量部をブレンダーで混合後、110℃で5時間乾燥し、径30mmφのベント式二軸押出機[(株)日本製鋼所製TEX30XSST]に供給し、シリンダー温度250℃、スクリュー回転数250rpm、吐出量9kg/h、およびベント減圧度3kPaで溶融押出してペレット化し、ステレオコンプレックスポリ乳酸−1を得た。得られたステレオコンプレックスポリ乳酸−1の重量平均分子量は13万、ガラス転移点(Tg)58℃、コンプレックス相ポリ乳酸結晶融解ピーク温度(Tms)は220℃、カルボキシル基含有量は17eq/ton、エナンチオマー平均連鎖長は28、示差走査熱量計(DSC)測定の昇温過程における融解ピークのうち195℃以上の融解ピークの割合が100%であった。なおNA−11の添加量はPLLA1,PDLA1の合計100重量部あたりの重量部である。
[A-α-3-1 component: production of stereocomplex polylactic acid-1 (scPLA-1)]
[Production Example 3-1]
100 parts by weight of polylactic acid resin composed of 50 parts by weight of PLLA and PDLA obtained in Production Examples 1 and 2 and sodium 2,2′-methylenebis (4,6-di-tert-butylphenyl) phosphate (Adekastab) (NA-11: manufactured by ADEKA Co., Ltd.) 0.1 parts by weight was mixed with a blender, dried at 110 ° C. for 5 hours, and supplied to a vent type twin-screw extruder having a diameter of 30 mmφ [TEX30XSST manufactured by Nippon Steel Works, Ltd.] Then, it was melt-extruded and pelletized at a cylinder temperature of 250 ° C., a screw rotation speed of 250 rpm, a discharge rate of 9 kg / h, and a vent vacuum of 3 kPa to obtain stereocomplex polylactic acid-1. The resulting stereocomplex polylactic acid-1 had a weight average molecular weight of 130,000, a glass transition point (Tg) of 58 ° C., a complex phase polylactic acid crystal melting peak temperature (Tms) of 220 ° C., and a carboxyl group content of 17 eq / ton, The average enantiomeric chain length was 28, and the ratio of melting peaks at 195 ° C. or higher was 100% among the melting peaks in the temperature rising process of differential scanning calorimetry (DSC) measurement. The amount of NA-11 added is part by weight per 100 parts by weight of PLLA1 and PDLA1 in total.
[A−α−3−2成分:ステレオコンプレックスポリ乳酸−2の製造(scPLA−2)]
[製造例3−2]
製造例1および2で使用したジ−n−ヘキシルホスホノ酢酸エチル0.082重量部を、1重量部に変えた以外は、製造例1および2と同様に方法で得られたPLLAとPDLAを用い、製造例3−1と同様な方法でステレオコンプレックスポリ乳酸−2を製造した。得られたステレオコンプレックスポリ乳酸−2の重量平均分子量は12.5万、ガラス転移点(Tg)58℃、コンプレックス相ポリ乳酸結晶融解ピーク温度(Tms)は222℃、カルボキシル基含有量は45eq/ton、エナンチオマー平均連鎖長は27、示差走査熱量計(DSC)測定の昇温過程における融解ピークのうち195℃以上の融解ピークの割合が100%であった。なおNA−11の添加量はPLLA1,PDLA1の合計100重量部あたりの重量部である。
[Component A-α-3-2: Production of stereocomplex polylactic acid-2 (scPLA-2)]
[Production Example 3-2]
The PLLA and PDLA obtained by the same method as in Production Examples 1 and 2 except that 0.082 parts by weight of ethyl di-n-hexylphosphonoacetate used in Production Examples 1 and 2 were changed to 1 part by weight. The stereocomplex polylactic acid-2 was produced in the same manner as in Production Example 3-1. The resulting stereocomplex polylactic acid-2 had a weight average molecular weight of 125,000, a glass transition point (Tg) of 58 ° C., a complex phase polylactic acid crystal melting peak temperature (Tms) of 222 ° C., and a carboxyl group content of 45 eq / The average chain length of ton and enantiomer was 27, and the ratio of the melting peak at 195 ° C. or higher among the melting peaks in the temperature rising process of differential scanning calorimetry (DSC) was 100%. The amount of NA-11 added is part by weight per 100 parts by weight of PLLA1 and PDLA1 in total.
[A−α−3−3成分:ステレオコンプレックスポリ乳酸−3の製造(scPLA−3)]
[製造例3−3]
製造例1および2で使用したジ−n−ヘキシルホスホノ酢酸エチル0.082重量部を、まったく添加しないとした以外は、製造例1および2と同様に方法で得られたPLLAとPDLAを用い、製造例3−1と同様な方法でステレオコンプレックスポリ乳酸−3を製造した。得られたステレオコンプレックスポリ乳酸−3の重量平均分子量は12.7万、ガラス転移点(Tg)58℃、コンプレックス相ポリ乳酸結晶融解ピーク温度(Tms)は221℃、カルボキシル基含有量は28eq/ton、エナンチオマー平均連鎖長は28、示差走査熱量計(DSC)測定の昇温過程における融解ピークのうち195℃以上の融解ピークの割合が100%であった。なおNA−11の添加量はPLLA1,PDLA1の合計100重量部あたりの重量部である。結果をまとめて表1中に記載する。
[A-α-3-3 component: production of stereocomplex polylactic acid-3 (scPLA-3)]
[Production Example 3-3]
Using PLLA and PDLA obtained by the same method as in Production Examples 1 and 2, except that 0.082 parts by weight of ethyl di-n-hexylphosphonoacetate used in Production Examples 1 and 2 was not added at all. Stereocomplex polylactic acid-3 was produced in the same manner as in Production Example 3-1. The resulting stereocomplex polylactic acid-3 had a weight average molecular weight of 1270, a glass transition point (Tg) of 58 ° C., a complex phase polylactic acid crystal melting peak temperature (Tms) of 221 ° C., and a carboxyl group content of 28 eq / The average chain length of ton and enantiomer was 28, and the ratio of the melting peak at 195 ° C. or higher among the melting peaks in the temperature rising process of differential scanning calorimetry (DSC) measurement was 100%. The amount of NA-11 added is part by weight per 100 parts by weight of PLLA1 and PDLA1 in total. The results are summarized in Table 1.
2.組成物ペレットの製造および評価
下記の実施例、比較例に示す方法により、組成物ペレットの製造を行った。また実施例中における各値は下記の方法で求めた。
2. Production and Evaluation of Composition Pellet Composition pellets were produced by the methods shown in the following Examples and Comparative Examples. Moreover, each value in an Example was calculated | required with the following method.
(1)エナンチオマー平均連鎖長
組成物を射出成形機(東芝機械(株)製:IS−150EN)を使用して、シリンダー温度230℃、金型温度50℃にて、長さ130mm、幅13mm、厚さ1.5mmの成形片を成形した。こうして得られた成形片を、前述の方法でエナンチオマー平均連鎖長を算出した。
(1) Enantiomeric average chain length The composition was injected using an injection molding machine (Toshiba Machine Co., Ltd .: IS-150EN) at a cylinder temperature of 230 ° C. and a mold temperature of 50 ° C., a length of 130 mm, a width of 13 mm, A molded piece having a thickness of 1.5 mm was formed. The enantiomeric average chain length of the molded piece thus obtained was calculated by the method described above.
(2)湿熱後の寸法変化
組成物を射出成形機(東芝機械(株)製:IS−150EN)を使用して、シリンダー温度230℃、金型温度50℃、成形サイクル100秒にて成形した、長さ150mm、幅150mm、厚さ1.0mmの平板成形片の片端のみを固定した状態で、70℃×60%RH×500時間の条件で湿熱処理し、湿熱処理前後で発生した平板の反りを市販のノギスを用いて測定し、以下基準に従って判定した。なお、ここで言う成形サイクルTとは、射出時間、保圧時間、冷却時間の合計である。
○:湿熱処理前後の平板の反りが、0.5cm未満
△:湿熱処理前後の平板の反りが、0.5cm以上、1.0cm未満
×:湿熱処理前後の平板の反りが、1.0cm以上
(2) Dimensional change after wet heat The composition was molded using an injection molding machine (Toshiba Machine Co., Ltd .: IS-150EN) at a cylinder temperature of 230 ° C, a mold temperature of 50 ° C, and a molding cycle of 100 seconds. In a state where only one end of a flat plate molded piece having a length of 150 mm, a width of 150 mm, and a thickness of 1.0 mm is fixed, wet heat treatment is performed under conditions of 70 ° C. × 60% RH × 500 hours, and the flat plate generated before and after the wet heat treatment The warpage was measured using a commercially available caliper and judged according to the following criteria. The molding cycle T referred to here is the total of the injection time, the pressure holding time, and the cooling time.
○: The warpage of the flat plate before and after the wet heat treatment is less than 0.5 cm Δ: The warpage of the flat plate before and after the wet heat treatment is 0.5 cm or more and less than 1.0 cm ×: The warpage of the flat plate before and after the wet heat treatment is 1.0 cm or more
(3)湿熱処理後の引張強度保持率(ΔTYratio−1)
組成物を射出成形機(東芝機械(株)製:IS−150EN)を使用して、シリンダー温度230℃、金型温度50℃、成形サイクル100秒にて、厚み4mmのISO規格に準拠した試験片を成形した。該試験片を温度80℃、相対湿度95%の恒温恒湿試験機に100時間放置して処理した後、温度23℃、相対湿度50%の環境下で24時間放置した試験片(湿熱処理後の試験片)を用いて測定した引張強度と、温度23℃、相対湿度50%の環境下で24時間放置した試験片(湿熱処理前の試験片)を用いて測定した引張強度を、下記数式にしたがって計算し、湿熱処理後の引張強度保持率(ΔTYratio−1)を算出した。
ΔTYratio−1=100×(湿熱処理後の試験片の引張強度)/(湿熱処理前の試験片の引張強度)
なお、ここで言う引張強度とは、引張破断強度と引張降伏強度のうち、強度が高い方の強度を指す。
(3) Tensile strength retention after wet heat treatment (ΔTYratio-1)
The composition was tested using an injection molding machine (Toshiba Machine Co., Ltd .: IS-150EN) at a cylinder temperature of 230 ° C., a mold temperature of 50 ° C., and a molding cycle of 100 seconds in accordance with the ISO standard with a thickness of 4 mm. A piece was molded. The test piece was left to stand for 100 hours in a constant temperature and humidity tester having a temperature of 80 ° C. and a relative humidity of 95%, and then left for 24 hours in an environment of a temperature of 23 ° C. and a relative humidity of 50% (after wet heat treatment). And the tensile strength measured using a test piece (test piece before wet heat treatment) left for 24 hours in an environment of a temperature of 23 ° C. and a relative humidity of 50%. The tensile strength retention (ΔTYratio-1) after the wet heat treatment was calculated.
ΔTYratio-1 = 100 × (tensile strength of test piece after wet heat treatment) / (tensile strength of test piece before wet heat treatment)
In addition, the tensile strength said here points out the intensity | strength with the higher intensity | strength among tensile breaking strength and tensile yield strength.
(4)滞留成形後の引張強度保持率(ΔTYratio−2)
組成物を射出成形機(東芝機械(株)製:IS−150EN)を使用して、シリンダー温度230℃、金型温度50℃、成形サイクル100秒にて成形した、厚み4mmのISO規格に準拠した試験片(通常成形の試験片)と、成形サイクル100秒で成形した後、温度を保持したまま成形機を10分間停止し、再度成形サイクル100秒で成形した、厚み4mmのISO規格に準拠した試験片(滞留成形の試験片)を、温度23℃、相対湿度50%の環境下で24時間放置した後、引張試験に供し、測定した引張強度を下記数式にしたがって計算し、滞留成形後の引張強度保持率(ΔTYratio−2)を算出した。
ΔTYratio−2=100×(滞留成形の試験片の引張強度)/(通常成形の試験片の引張強度)
なお、ここで言う引張強度とは、引張破断強度と引張降伏強度のうち、強度が高い方の強度を指す。
(4) Tensile strength retention after retention molding (ΔTYratio-2)
The composition was molded using an injection molding machine (Toshiba Machine Co., Ltd .: IS-150EN) at a cylinder temperature of 230 ° C., a mold temperature of 50 ° C., and a molding cycle of 100 seconds. The test piece (normally formed test piece) was molded with a molding cycle of 100 seconds, then the molding machine was stopped for 10 minutes while maintaining the temperature, and molded again with a molding cycle of 100 seconds. The test piece (residual molding test piece) was allowed to stand for 24 hours in an environment at a temperature of 23 ° C. and a relative humidity of 50%, and then subjected to a tensile test, and the measured tensile strength was calculated according to the following formula. The tensile strength retention ratio (ΔTYratio-2) of was calculated.
ΔTYratio-2 = 100 × (tensile strength of staying molded specimen) / (tensile strength of normal molded specimen)
In addition, the tensile strength said here points out the intensity | strength with the higher intensity | strength among tensile breaking strength and tensile yield strength.
(5)金型汚れ評価
組成物を射出成形機(東芝機械(株)製:IS−150EN)を使用して、シリンダー温度230℃、金型温度50℃、成形サイクル100秒にて長さ130mm、幅13mm、厚さ1.5mmの成形片を500ショット成形し、その前後の金型表面の状態を目視で観察し、下記のように評価した。
○ : 連続成形試験の前後において変化なし
△ : 連続成形試験後にかなり付着物あり
× : 連続成形試験後に付着物が非常に多い
なお、A成分としては上記記載のA−1、A−2、A−3−1〜3、B成分としては参考例記載のDHPA(B−1成分)と比較用として次亜リン酸アンモニウム[試薬](B−2成分)、C成分としては製造例3−1−1記載のNA−11を用い、その他の原料としては、以下のものを用いた。
(5) Evaluation of mold fouling Using an injection molding machine (Toshiba Machine Co., Ltd .: IS-150EN), the composition is 130 mm in length at a cylinder temperature of 230 ° C., a mold temperature of 50 ° C., and a molding cycle of 100 seconds. A molded piece having a width of 13 mm and a thickness of 1.5 mm was molded into 500 shots, and the state of the mold surface before and after that was visually observed and evaluated as follows.
○: No change before and after the continuous molding test △: There is a considerable amount of deposit after the continuous molding test ×: Very much deposit after the continuous molding test As the A component, A-1, A-2, A described above As 3-1 to 3 and B component, DHPA (B-1 component) described in Reference Example and ammonium hypophosphite [reagent] (B-2 component) for comparison, and as C component, Production Example 3-1 NA-11 described in -1 was used, and the following were used as other raw materials.
(6)難燃性
組成物を射出成形機(東芝機械(株)製:IS−150EN)を使用して、シリンダー温度230℃、金型温度50℃、成形サイクル100秒にて成形した、長さ130mm、幅13mm、厚さ2.0mmの成形片を成形し、米国アンダーライターラボラトリー社の定める方法(UL94)により、試験片厚さ2.0mmにおける難燃性を評価した。
(6) Flame retardance The composition was molded using an injection molding machine (Toshiba Machine Co., Ltd .: IS-150EN) at a cylinder temperature of 230 ° C, a mold temperature of 50 ° C, and a molding cycle of 100 seconds. A molded piece having a thickness of 130 mm, a width of 13 mm, and a thickness of 2.0 mm was molded, and the flame retardancy at a test piece thickness of 2.0 mm was evaluated by a method (UL94) defined by US Underwriter Laboratory.
(7)ノッチ付衝撃値
組成物を射出成形機(東芝機械(株)製:IS−150EN)を使用して、シリンダー温度230℃、金型温度50℃、成形サイクル100秒にて、厚み4mmのISO規格に準拠した試験片を成形し、温度23℃、相対湿度50%の環境下で24時間放置した後、ISO規格に準拠してノッチ付衝撃値を測定した。
(7) Impact value with notch Using an injection molding machine (manufactured by Toshiba Machine Co., Ltd .: IS-150EN), the cylinder temperature is 230 ° C., the mold temperature is 50 ° C., the molding cycle is 100 seconds, and the thickness is 4 mm. A test piece conforming to the ISO standard was molded and allowed to stand for 24 hours in an environment of a temperature of 23 ° C. and a relative humidity of 50%, and then an impact value with a notch was measured according to the ISO standard.
(A−β成分:メタクリル系樹脂)
PMMA:メタクリル樹脂(三菱レイヨン(株)製アクリペットVH、重量平均分子量10万、ガラス転移温度105℃、MVR[240℃、2.16kg]=2(cm3/10分)
(D成分:酸化防止剤)
D−1成分:ホスファイト系酸化防止剤((株)ADEKA製アデカスタブPEP24G(商品名))
D−2成分:ヒンダードフェノール系酸化防止剤(チバ・スペシャルティ・ケミカルズ製:Irganox1076(商品名))
(E成分:末端封鎖剤)
E−1:脂肪族系ポリカルボジイミド(日清紡(株)製 カルボジライトLA−1(商品名))
E−2:エポキシ基含有アクリル−スチレン共重合体(BASFジャパン(株)製 ADR−4368CS(商品名))
(F成分:衝撃改質剤)
F−1成分:アクリル系コアシェルゴム(三菱レイヨン(株)製:メタブレンW450A(商品名))
F−2成分:共重合ポリエチレン(住友化学(株)製:ボンドファスト7M(商品名))
(G成分:難燃剤)
G−1成分:リン酸エステル系難燃剤 大八化学工業(株)製 PX−200 [レゾルシノールビス(ジ−2,6−キシリルホスフェート)]
G−2成分:ホスフィン酸塩系難燃剤 クラリアントジャパン(株)製 EXOLIT1240 [ジエチルホスフィン酸アルミニウム]
(H成分:無機系充填剤)
H−1:タルク(日本タルク(株)製 P−3[平均粒径5μm](商品名))
H−2:ガラス繊維(日東紡(株)製 3PE−937S[平均径13μm、カット長3mmのチョップドストランド](商品名))
(J成分:滴下防止剤)
J−1:フィブリル形成能を有する含フッ素ポリマー(ダイキン化学工業(株)のポリフロンMPA FA500(商品名))
(A-β component: methacrylic resin)
PMMA: methacrylic resin (Mitsubishi Rayon Co., Ltd. ACRYPET VH, weight average molecular weight of 100,000, a glass transition temperature of 105 ℃, MVR [240 ℃, 2.16kg] = 2 (cm 3/10 min)
(D component: antioxidant)
D-1 component: Phosphite type antioxidant (Adeka ADEKA STAB PEP24G (trade name))
Component D-2: hindered phenol antioxidant (Ciba Specialty Chemicals: Irganox 1076 (trade name))
(E component: terminal blocking agent)
E-1: Aliphatic polycarbodiimide (Carbodilite LA-1 (trade name) manufactured by Nisshinbo Co., Ltd.)
E-2: Epoxy group-containing acrylic-styrene copolymer (ADR-4368CS (trade name) manufactured by BASF Japan K.K.)
(F component: impact modifier)
F-1 component: Acrylic core shell rubber (Mitsubishi Rayon Co., Ltd. product: Metabrene W450A (trade name))
F-2 component: Copolyethylene (Sumitomo Chemical Co., Ltd .: Bondfast 7M (trade name))
(G component: flame retardant)
G-1 component: Phosphate ester flame retardant Daihachi Chemical Industry Co., Ltd. PX-200 [resorcinol bis (di-2,6-xylyl phosphate)]
G-2 component: Phosphinate flame retardant EXOLIT1240 [Aluminum diethylphosphinate] manufactured by Clariant Japan Co., Ltd.
(H component: inorganic filler)
H-1: Talc (Nippon Talc Co., Ltd. P-3 [average particle diameter 5 μm] (trade name))
H-2: Glass fiber (manufactured by Nittobo Co., Ltd. 3PE-937S [chopped strand having an average diameter of 13 μm and a cut length of 3 mm] (trade name))
(J component: anti-dripping agent)
J-1: Fluoropolymer having fibril-forming ability (Polyflon MPA FA500 (trade name) from Daikin Chemical Industries, Ltd.)
<実施例1〜7、比較例1〜10>
ポリ乳酸樹脂として製造例1、2、3−1〜3−3で製造したポリ乳酸樹脂A−α−1、A−α−2、A−α−3−1〜A−α−3−3成分を用いて、表2〜3の組成のうちH−2を除く組成をドライブレンドにて均一に予備混合した後、かかる予備混合物を第1供給口より供給し、F−2成分を第二供給口から供給し、溶融押出してペレット化した。ここで、第一供給口とは根元の供給口、第二供給口とはサイドスクリュウに備え付けた供給口のことである。なお、F−2成分が組成に含まれない場合は、第1供給口からのみの供給となることは言うまでもない。溶融押出は、サイドスクリューを備えた径30mmφのベント式二軸押出機[(株)日本製鋼所製TEX30XSST]を用い実施した。また、押出温度は、C1/C2〜C5/C6/C7〜C11/D=10℃/240℃/230℃/220℃/220℃とし、メインスクリュー回転数は150rpm、サイドスクリュー回転数は50rpm、吐出量は20kg/h、ベント減圧度は3kPaとした。
得られたペレットを100℃で5時間、熱風循環式乾燥機により乾燥し、射出成形機(東芝機械(株)製:IS−150EN)にて成形し、成形サイクル、成形品の割れ、色むら、曲げ弾性率、荷重たわみ温度、難燃性の評価を実施した。
<Examples 1-7, Comparative Examples 1-10>
Polylactic acid resins A-α-1, A-α-2, A-α-3-1 to A-α-3-3 produced in Production Examples 1, 2, 3-1 to 3-3 as polylactic acid resins The components except for H-2 among the compositions in Tables 2 to 3 were premixed uniformly by dry blending using the components, and then the premixed mixture was supplied from the first supply port, and the F-2 component was added to the second component. It supplied from the supply port, melt-extruded, and pelletized. Here, the first supply port is a base supply port, and the second supply port is a supply port provided to the side screw. In addition, when F-2 component is not contained in a composition, it cannot be overemphasized that it becomes supply only from a 1st supply port. The melt extrusion was carried out using a vent type twin screw extruder [TEX30XSST manufactured by Nippon Steel Works, Ltd.] with a diameter of 30 mmφ equipped with a side screw. The extrusion temperature is C1 / C2-C5 / C6 / C7-C11 / D = 10 ° C./240° C./230° C./220° C./220° C., the main screw rotation speed is 150 rpm, the side screw rotation speed is 50 rpm, The discharge rate was 20 kg / h, and the vent pressure reduction was 3 kPa.
The obtained pellets were dried with a hot air circulation dryer at 100 ° C. for 5 hours and molded with an injection molding machine (manufactured by Toshiba Machine Co., Ltd .: IS-150EN), molding cycle, cracks in molded product, uneven color. The bending elastic modulus, the deflection temperature under load, and the flame retardance were evaluated.
<実施例1〜6>
本発明記載の範囲でA〜E、H成分を含む組成物は、湿熱処理時や滞留成形時の物性低下が小さく、優れた特性を有する。なお、エナンチオマー連鎖長が10〜40の範囲内である実施例3〜6は湿熱後の寸法変化が小さく、優れた寸法安定性を示した。B成分を工程(ii)で添加した実施例3は、B成分を工程(i)で添加した実施例4や5に比べ、物性保持率が高く、金型汚れも少ない、特に優れた組成物であり、作業時の悪臭も全く無い良好な組成物であった。
<Examples 1-6>
The composition containing the components A to E and H within the range described in the present invention has excellent properties with little deterioration in physical properties during wet heat treatment or retention molding. In addition, Examples 3-6 in which the enantiomer chain length is within the range of 10-40 showed a small dimensional change after wet heat and showed excellent dimensional stability. Example 3 in which component B was added in step (ii) was a particularly excellent composition having a higher physical property retention rate and less mold fouling than Examples 4 and 5 in which component B was added in step (i). It was a good composition with no bad odor during work.
<実施例7>
実施例3に、衝撃改質剤(F成分)とG成分(難燃剤)を本発明記載の範囲で更に配合した実施例7は、湿熱処理時や滞留成形時の物性低下が少なく、且つ湿熱後の寸法変化も小さく良好であった。また優れた難燃性と耐衝撃性を有する実用上有益な特性を示した。
<Example 7>
Example 7, in which an impact modifier (F component) and a G component (flame retardant) were further blended with Example 3 within the range described in the present invention, had little deterioration in physical properties during wet heat treatment or residence molding, The subsequent dimensional change was small and good. It also showed practically beneficial properties with excellent flame retardancy and impact resistance.
<比較例1>
A−β成分が配合されていない比較例1は、実施例3に比べて湿熱後の寸法変化が大きいため、実用上好ましくない。
<Comparative Example 1>
Since Comparative Example 1 in which the A-β component is not blended has a large dimensional change after wet heat as compared with Example 3, it is not practically preferable.
<比較例2、3>
B成分の添加量が請求範囲外である比較例2、3は、実施例3に比べ、湿熱処理時や滞留成形時の物性低下が大きく、好ましくない。特に比較例3はB−1成分が請求の範囲を超えて含まれているため、金型汚染が激しく、作業環境時の悪臭も目立った。
<Comparative Examples 2 and 3>
Comparative Examples 2 and 3 in which the amount of component B added is outside the scope of claims are not preferable, as compared to Example 3, because the physical properties are greatly reduced during wet heat treatment and during residence molding. In particular, Comparative Example 3 contained B-1 component beyond the scope of the claims, so the mold contamination was severe, and the bad odor during the working environment was conspicuous.
<比較例4>
特定化合物以外のB成分を用いた比較例4は、実施例3に比べて湿熱処理時や滞留成形時の物性低下が大きく、ポリ乳酸中の残留触媒を効果的に失活していないと言える。
<Comparative example 4>
Compared to Example 3, Comparative Example 4 using a component B other than the specific compound has a large decrease in physical properties during wet heat treatment or retention molding, and it can be said that the residual catalyst in polylactic acid is not effectively deactivated. .
<比較例5>
C成分の添加量が請求範囲外である比較例5は、実施例3に比べて湿熱後の寸法変化が大きく、また湿熱処理時や滞留成形時の物性低下も見られ、好ましくない。
<Comparative Example 5>
Comparative Example 5 in which the amount of component C added is outside the scope of the claims is not preferable because the dimensional change after wet heat is larger than that of Example 3, and the physical properties are reduced during wet heat treatment or stay molding.
<比較例6>
C成分が含まれていない比較例6は実施例3に比べて湿熱後の寸法変化が大きくまた、湿熱処理時や滞留成形時の物性低下も見られ、実用上好ましくない。
<Comparative Example 6>
In Comparative Example 6 containing no C component, the dimensional change after wet heat is larger than that in Example 3, and the physical properties are lowered during wet heat treatment or stay molding.
<比較例7、8>
D成分の添加量が請求範囲外である比較例7、8は、実施例3に比べ、湿熱処理時や滞留成形時の物性低下が大きく、好ましくない。特に比較例8はD成分が請求の範囲を超えて含まれているため、金型汚染が激しく、作業環境時の悪臭も目立った。
<Comparative Examples 7 and 8>
Comparative Examples 7 and 8 in which the amount of component D added is outside the scope of claims are not preferable because, as compared with Example 3, the physical properties are greatly reduced during wet heat treatment or stay molding. In particular, since Comparative Example 8 contains the D component beyond the scope of claims, the mold was heavily contaminated and the bad odor during the working environment was conspicuous.
<比較例9、10>
E成分の添加量が請求範囲外である比較例9、10は、実施例3に比べ、湿熱処理時や滞留成形時の物性低下が大きく、好ましくない。特に比較例10はE成分が請求の範囲を超えて含まれているため、金型汚染が激しく、作業環境時の悪臭も目立った。
<Comparative Examples 9 and 10>
Comparative Examples 9 and 10 in which the amount of the E component added is outside the scope of claims are not preferable because, compared with Example 3, the physical properties are greatly reduced during wet heat treatment and during residence molding. In particular, since Comparative Example 10 contained the E component beyond the scope of claims, the mold was severely contaminated and the bad odor during the working environment was conspicuous.
本発明のポリ乳酸組成物は、自動車部品、電気・電子部品、電気機器外装部品、OA外装部品等の材料として有用である。 The polylactic acid composition of the present invention is useful as a material for automobile parts, electrical / electronic parts, electrical equipment exterior parts, OA exterior parts, and the like.
Claims (18)
0.001〜5重量部のホスホノ脂肪酸エステル(B成分)、
0.01〜5重量部のリン酸エステル金属塩(C成分)、
0.001〜2重量部の、ホスファイト系化合物、ホスホナイト系化合物、ヒンダートフェノール系化合物およびチオエーテル系化合物からなる群より選ばれる少なくとも一種の酸化防止剤(D成分)、並びに
0.001〜10重量部の末端封鎖剤(E成分)、
を含有する組成物。 100 parts by weight of a resin component (component A) comprising 5 to 95% by weight of polylactic acid (A-α component) and 95 to 5% by weight of a methacrylic resin (A-β component),
0.001 to 5 parts by weight of a phosphono fatty acid ester (component B),
0.01-5 parts by weight of a phosphate metal salt (component C),
0.001 to 2 parts by weight of at least one antioxidant (D component) selected from the group consisting of phosphite compounds, phosphonite compounds, hindered phenol compounds and thioether compounds, and 0.001 to 10 Parts by weight of end-capping agent (E component),
A composition containing
T(%)=t1/t0×100
(但し、t0は初期引張強度、t1は80℃、95%RH雰囲気下、100時間後の引張強度)。 The composition according to any one of claims 1 to 11, wherein the tensile strength retention (T) represented by the following formula is 60% or more.
T (%) = t 1 / t 0 × 100
(Where t 0 is the initial tensile strength, and t 1 is the tensile strength after 100 hours in an atmosphere of 80 ° C. and 95% RH).
(ii) 得られたステレオコンプレックスポリ乳酸5〜95wt%とメタクリル系樹脂(A−β成分)95〜5wt%からなる樹脂成分100重量部に対し、0.001〜2重量部のホスホノ脂肪酸エステル(B成分)、0.001〜2重量部の、ホスファイト系化合物、ホスホナイト系化合物、ヒンダートフェノール系化合物、チオエーテル系化合物からなる群より選ばれる少なくとも一種の酸化防止剤(D成分)、並びに0.001〜10重量部の末端封鎖剤(E成分)を溶融混練する工程、
からなる請求項1〜14のいずれか一項に記載の組成物の製造方法。 (I) Composition-1 containing 0.001 to 3 parts by weight of phosphono fatty acid ester (component B) and 100 parts by weight of poly-L lactic acid (A-α-1 component) Composition-2 containing 0.001 to 3 parts by weight of phosphono fatty acid ester (component B) with respect to poly-D lactic acid (component A-α-2) A step of preparing stereocomplex polylactic acid by melt-kneading in the presence of 0.01 to 5 parts by weight of a phosphoric acid ester metal salt (component C) with respect to a total of 100 parts by weight; and (ii) the obtained stereo 0.001 to 2 parts by weight of a phosphono fatty acid ester (component B), 0.001 with respect to 100 parts by weight of a resin component comprising 5 to 95 wt% of complex polylactic acid and 95 to 5 wt% of a methacrylic resin (A-β component) ~ 2 weight At least one antioxidant (D component) selected from the group consisting of phosphite compounds, phosphonite compounds, hindered phenol compounds, thioether compounds, and 0.001 to 10 parts by weight of an end-blocking agent ( A step of melt-kneading E component),
The manufacturing method of the composition as described in any one of Claims 1-14 which consists of.
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