JP2009275126A - 難燃性樹脂組成物 - Google Patents
難燃性樹脂組成物 Download PDFInfo
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- JP2009275126A JP2009275126A JP2008128159A JP2008128159A JP2009275126A JP 2009275126 A JP2009275126 A JP 2009275126A JP 2008128159 A JP2008128159 A JP 2008128159A JP 2008128159 A JP2008128159 A JP 2008128159A JP 2009275126 A JP2009275126 A JP 2009275126A
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- retardant resin
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- 239000011342 resin composition Substances 0.000 title claims abstract description 80
- 239000003063 flame retardant Substances 0.000 title claims abstract description 61
- 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 title claims abstract description 58
- 229920001955 polyphenylene ether Polymers 0.000 claims abstract description 81
- 239000002245 particle Substances 0.000 claims abstract description 63
- -1 aromatic vinyl compound Chemical class 0.000 claims description 82
- 229920002554 vinyl polymer Polymers 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 42
- 239000003381 stabilizer Substances 0.000 claims description 34
- 229920001577 copolymer Polymers 0.000 claims description 29
- 229920001400 block copolymer Polymers 0.000 claims description 28
- 239000002904 solvent Substances 0.000 claims description 28
- 229920000642 polymer Polymers 0.000 claims description 19
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 17
- 239000000243 solution Substances 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 150000002500 ions Chemical class 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000004952 Polyamide Substances 0.000 claims description 11
- 229920002647 polyamide Polymers 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 10
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 229920005992 thermoplastic resin Polymers 0.000 claims description 9
- 229910052698 phosphorus Inorganic materials 0.000 claims description 8
- 239000011574 phosphorus Substances 0.000 claims description 8
- 229920001971 elastomer Polymers 0.000 claims description 7
- 239000000806 elastomer Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000010298 pulverizing process Methods 0.000 claims description 7
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 229920000106 Liquid crystal polymer Polymers 0.000 claims description 5
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims description 5
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 claims description 4
- UEOYYXOZJDMHDD-UHFFFAOYSA-N 2-(dodecylsulfanylmethyl)prop-2-enoic acid methane Chemical compound C.C=C(C(=O)O)CSCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCC UEOYYXOZJDMHDD-UHFFFAOYSA-N 0.000 claims description 4
- LHYYOWUBDGZMDK-UHFFFAOYSA-N 2-methyl-4,6-bis(octadecylsulfanylmethyl)phenol Chemical compound CCCCCCCCCCCCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCCCCCCCCCCCC)=C1 LHYYOWUBDGZMDK-UHFFFAOYSA-N 0.000 claims description 4
- GAODDBNJCKQQDY-UHFFFAOYSA-N 2-methyl-4,6-bis(octylsulfanylmethyl)phenol Chemical compound CCCCCCCCSCC1=CC(C)=C(O)C(CSCCCCCCCC)=C1 GAODDBNJCKQQDY-UHFFFAOYSA-N 0.000 claims description 4
- VSAWBBYYMBQKIK-UHFFFAOYSA-N 4-[[3,5-bis[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-2,4,6-trimethylphenyl]methyl]-2,6-ditert-butylphenol Chemical compound CC1=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C(CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)C(C)=C1CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VSAWBBYYMBQKIK-UHFFFAOYSA-N 0.000 claims description 4
- VDBOZTHCRVHFSS-UHFFFAOYSA-N C.C=C(C(=O)O)CSCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCC Chemical compound C.C=C(C(=O)O)CSCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCC VDBOZTHCRVHFSS-UHFFFAOYSA-N 0.000 claims description 4
- UAIFVCXFYYZLQP-UHFFFAOYSA-N C.C=C(C(=O)O)CSCCCCCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCCCCCC Chemical compound C.C=C(C(=O)O)CSCCCCCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCCCCCC.C=C(C(=O)O)CSCCCCCCCCCCCCCCCCCC UAIFVCXFYYZLQP-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 claims description 4
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 4
- 239000004695 Polyether sulfone Substances 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 239000011572 manganese Substances 0.000 claims description 4
- 150000002829 nitrogen Chemical class 0.000 claims description 4
- 229920002492 poly(sulfone) Polymers 0.000 claims description 4
- 229920001230 polyarylate Polymers 0.000 claims description 4
- 229920006393 polyether sulfone Polymers 0.000 claims description 4
- 229920002530 polyetherether ketone Polymers 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- JOISCPZYGOECQA-UHFFFAOYSA-N 3-tert-butyl-5-methylphenol Chemical compound CC1=CC(O)=CC(C(C)(C)C)=C1 JOISCPZYGOECQA-UHFFFAOYSA-N 0.000 claims description 3
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 3
- 229920002292 Nylon 6 Polymers 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 3
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052797 bismuth Inorganic materials 0.000 claims description 3
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 3
- 229910052748 manganese Inorganic materials 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 230000001376 precipitating effect Effects 0.000 claims description 3
- SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 claims description 2
- CXZVXONURWPSCQ-UHFFFAOYSA-N 4-[[4,6-bis(octylsulfanyl)-1,3,5-triazin-2-yl]amino]phenol Chemical compound CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=CC(O)=CC=2)=N1 CXZVXONURWPSCQ-UHFFFAOYSA-N 0.000 claims description 2
- OKOBUGCCXMIKDM-UHFFFAOYSA-N Irganox 1098 Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NCCCCCCNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 OKOBUGCCXMIKDM-UHFFFAOYSA-N 0.000 claims description 2
- XAQKFOUWWAKVCH-UHFFFAOYSA-N OP(O)OP(O)O.C(C)(C)(C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)(C)C1=CC=CC=C1)C(O)C(CO)(CO)CO Chemical compound OP(O)OP(O)O.C(C)(C)(C1=CC=CC=C1)C1=C(C=CC(=C1)C(C)(C)C1=CC=CC=C1)C(O)C(CO)(CO)CO XAQKFOUWWAKVCH-UHFFFAOYSA-N 0.000 claims description 2
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 2
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 abstract description 15
- 239000002184 metal Substances 0.000 abstract description 15
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 abstract description 3
- 230000035939 shock Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 150000001875 compounds Chemical class 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000003822 epoxy resin Substances 0.000 description 17
- 229920000647 polyepoxide Polymers 0.000 description 17
- 238000012360 testing method Methods 0.000 description 16
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 14
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 239000004793 Polystyrene Substances 0.000 description 13
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 12
- 239000008188 pellet Substances 0.000 description 12
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- 238000002347 injection Methods 0.000 description 10
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- 229920002223 polystyrene Polymers 0.000 description 10
- 239000004721 Polyphenylene oxide Substances 0.000 description 9
- 239000003999 initiator Substances 0.000 description 9
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- KTLIMPGQZDZPSB-UHFFFAOYSA-M diethylphosphinate Chemical compound CCP([O-])(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-M 0.000 description 8
- 238000011144 upstream manufacturing Methods 0.000 description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 8
- 125000004018 acid anhydride group Chemical group 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 150000003949 imides Chemical class 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 229910000975 Carbon steel Inorganic materials 0.000 description 5
- XSAOTYCWGCRGCP-UHFFFAOYSA-K aluminum;diethylphosphinate Chemical compound [Al+3].CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC XSAOTYCWGCRGCP-UHFFFAOYSA-K 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
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- 125000002843 carboxylic acid group Chemical group 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 5
- 238000001125 extrusion Methods 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
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- 229920002545 silicone oil Polymers 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
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- 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 4
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 4
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- QRLSTWVLSWCGBT-UHFFFAOYSA-N 4-((4,6-bis(octylthio)-1,3,5-triazin-2-yl)amino)-2,6-di-tert-butylphenol Chemical compound CCCCCCCCSC1=NC(SCCCCCCCC)=NC(NC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=N1 QRLSTWVLSWCGBT-UHFFFAOYSA-N 0.000 description 2
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- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 2
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- 230000004580 weight loss Effects 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- PJEUXMXPJGWZOZ-UHFFFAOYSA-L zinc;diphenylphosphinate Chemical compound [Zn+2].C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1.C=1C=CC=CC=1P(=O)([O-])C1=CC=CC=C1 PJEUXMXPJGWZOZ-UHFFFAOYSA-L 0.000 description 1
- GYKKGOMJFMCRIN-UHFFFAOYSA-L zinc;ethyl(methyl)phosphinate Chemical compound [Zn+2].CCP(C)([O-])=O.CCP(C)([O-])=O GYKKGOMJFMCRIN-UHFFFAOYSA-L 0.000 description 1
- WMLXDIOQDFWKAO-UHFFFAOYSA-L zinc;methyl(phenyl)phosphinate Chemical compound [Zn+2].CP([O-])(=O)C1=CC=CC=C1.CP([O-])(=O)C1=CC=CC=C1 WMLXDIOQDFWKAO-UHFFFAOYSA-L 0.000 description 1
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Landscapes
- Injection Moulding Of Plastics Or The Like (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
【解決手段】
(A)ポリフェニレンエーテル及び(B)ホスフィン酸塩類を含む難燃性樹脂組成物であって、
前記(B)成分の数平均粒子径が0.01〜5μmであり、粒子径の小さい方から25%にあたる粒子の粒子径(d25)と75%にあたる粒子の粒子径(d75)の比(d75/d25)が1.0〜2.0である、樹脂組成物。
【選択図】なし
Description
ポリフェニレンエーテルの耐熱性を保持し、難燃性を向上させる技術として、ポリフェニレンエーテル/ポリスチレンにホスフィン酸塩を配合する技術(例えば、特許文献1、特許文献2参照)が提案されているが、耐熱性、金属腐食性等の観点ではまだ十分とは言えなかった。
また、ナノ粒状ホスフィン酸塩をポリマー中に混合し、難燃性、衝撃性を向上させる技術(例えば、特許文献3参照)が提案されているが、金属腐食性、外観等の観点では十分とは言えなかった。
[1]
(A)ポリフェニレンエーテル及び(B)ホスフィン酸塩類を含む難燃性樹脂組成物であって、
前記(B)成分の数平均粒子径が0.01〜5μmであり、粒子径の小さい方から25%にあたる粒子の粒子径(d25)と75%にあたる粒子の粒子径(d75)の比(d75/d25)が1.0〜2.0である、樹脂組成物。
[2]
前記(B)成分の最大粒子径が0.01〜20μmである、上記[1]記載の難燃性樹脂組成物。
[3]
前記(A)成分が溶解する溶媒(p)中に(A)成分を溶解させた溶液(p−A)と、前記(B)成分を溶解しない溶媒(q)中に(B)成分を分散させた溶液(q−B)と、を混合した後、前記(A)成分を溶解しない溶媒(r)を添加することにより析出させる工程を含む方法により得られる、上記[1]又は[2]記載の難燃性樹脂組成物(ここで、qとrは同種であっても異種であってもよい)。
[4]
前記(B)成分は、有機溶剤中で湿式粉砕して得られるホスフィン酸塩類である、上記[1]〜[3]のいずれか記載の難燃性樹脂組成物。
[5]
前記(B)成分は、下記式(i)及び/又は(ii)で示されるホスフィン酸塩類である、上記[1]〜[4]のいずれか記載の難燃性樹脂組成物。
[6]
(C)エラストマーをさらに含む、上記[1]〜[5]のいずれか記載の難燃性樹脂組成物。
[7]
前記(C)成分は、少なくとも1個の芳香族ビニル化合物を主体とする重合体ブロックと、少なくとも1個の共役ジエン化合物を主体とする重合体ブロックと、からなるブロック共重合体及び/又はその水素添加されたブロック共重合体である、上記[6]記載の難燃性樹脂組成物。
[8]
(D)安定剤をさらに含む、上記[1]〜[7]のいずれか記載の難燃性樹脂組成物。
[9]
前記(D)成分は、ヒンダードフェノール系安定剤、リン系安定剤、イオウ系安定剤からなる群から選ばれる1種以上である、上記[8]記載の難燃性樹脂組成物。
[10]
前記(D)成分は、ペンタエリスリトールテトラキス〔3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート〕、オクタデシル−3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート、N,N’−ヘキサン−1,6−ジイルビス[3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオンアミド]、1,3,5−トリメチル−2,4,6−トリス(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)ベンゼン、トリス(2,4−ジ−tert−ブチルフェニル)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{2,4−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、テトラキス〔メチレン−3−(ラウリルチオ)プロピオネート〕メタン、テトラキス〔メチレン−3−(ミリスチルチオ)プロピオネート〕メタン、テトラキス〔メチレン−3−(ステアリルチオ)プロピオネート〕メタン、4,6−ビス(オクチルチオメチル)−o−クレゾール、4,6−ビス(ステアリルチオメチル)−o−クレゾール、2,6−ジ−t−ブチル−4−{4,6−ビス(オクチルチオ)−1,3,5−トリアジン−2−イルアミノ}フェノール、4,4−チオビス(3−メチル−5−t−ブチルフェノール)よりなる群から選ばれる1種以上である、上記[8]又は[9]記載の難燃性樹脂組成物。
[11]
(E)(A)成分以外の熱可塑性樹脂をさらに含み、(A)成分と(E)成分の合計100質量%に対し、(A)成分1〜99質量%、(E)成分1〜99質量%である、上記[1]〜[10]のいずれか記載の難燃性樹脂組成物。
[12]
前記(E)成分は、芳香族ビニル化合物重合体、芳香族ビニル化合物共重合体、ポリプロピレン、ポリエチレン、ポリアミド6、ポリアミド66、ポリアミド66/6、芳香族環含有ポリアミド、脂肪族環含有ポリアミド、ポリフェニレンサルファイド、液晶ポリマー、ポリエーテルエーテルケトン、ポリアリレート、ポリエーテルサルフォン、ポリサルフォンから選ばれる1種以上である、上記[11]記載の難燃性樹脂組成物。
[13]
上記[1]〜[12]のいずれか記載の難燃性樹脂組成物からなる射出成形体。
[14]
上記[1]〜[12]のいずれか記載の難燃性樹脂組成物からなるシート。
(A)成分のポリフェニレンエーテルとは、式(1)の構造単位からなる、ホモ重合体及び/又は共重合体である。
(1)ラジカル開始剤の存在下又は非存在下で、100℃以上、ポリフェニレンエーテルのガラス転移温度未満の範囲の温度でポリフェニレンエーテルを溶融させることなく変性化合物と反応させる方法、
(2)ラジカル開始剤の存在下又は非存在下でポリフェニレンエーテルのガラス転移温度以上、360℃以下の範囲の温度で変性化合物と溶融混練し反応させる方法、
(3)ラジカル開始剤の存在下又は非存在下でポリフェニレンエーテルのガラス転移温度未満の温度で、ポリフェニレンエーテルと変性化合物を溶液中で反応させる方法、
等が挙げられ、これらいずれの方法でも構わない。
(1)ラジカル開始剤の存在下又は非存在下でブロック共重合体の軟化点温度以上250℃以下の範囲の温度で変性化合物と溶融混練し反応させる方法、
(2)ラジカル開始剤の存在下又は非存在下でブロック共重合体の軟化点以下の温度で、ブロック共重合体と変性化合物を溶液中で反応させる方法、
(3)ラジカル開始剤の存在下又は非存在下でブロック共重合体の軟化点以下の温度で、ブロック共重合体と変性化合物を溶融させることなく反応させる方法、
等が挙げられる。これらいずれの方法でも構わないが、(1)の方法が好ましく、更には(1)の中でもラジカル開始剤存在下で行う方法が特に好ましい。
(1)芳香族ビニル化合物、不飽和ジカルボン酸イミド誘導体及び必要に応じて、その他共重合可能なビニル化合物からなる混合物を共重合させる方法、
(2)芳香族ビニル化合物、不飽和ジカルボン酸無水物及び必要に応じて、その他共重合可能なビニル化合物からなる混合物を共重合させた後、アンモニア及び/又は第一級アミンを反応させて酸無水物基をイミド基に変換させる方法、等が挙げられる。
(使用した原料)
(1)(A)ポリフェニレンエーテル(以下、PPEと略記)
ポリ(2,6−ジメチル−1,4−フェニレンエーテル)
商品名:S201A(旭化成ケミカルズ社製)
特開2005−179362号公報の実施例に記載されている製法を参考にして、ジエチルホスフィン酸アルミニウム(DEP−1)を製造した。DEP−2〜DEP−5については、後述する製造例1及び製造例2のとおりに、DEP−1から製造した。
(2−1)DEP−1
数平均粒子径:1.7μm、最大粒子径:9.5μm、d75/d25:3.0
(2−2)DEP−2
数平均粒子径:0.20μm、最大粒子径:0.45μm、d75/d25:1.4
(2−3)DEP−3
数平均粒子径:0.52μm、最大粒子径:1.2μm、d75/d25:1.7
(2−4)DEP−4
数平均粒子径:1.4μm、最大粒子径:2.6μm、d75/d25:1.8
(2−5)DEP−5
数平均粒子径:0.23μm、最大粒子径:1.1μm、d75/d25:2.3
商品名:クレイトン(登録商標)G1651E(クレイトンポリマー社製)
商品名:PSJポリスチレン(登録商標)685(PSジャパン社製)
DEP−1をメタノール中に固体濃度30質量%となるように分散させ、湿式粉砕装置[スーパーアペックスミルUAM−015:寿工業社製]を用いて、0.1mmジルコニアビーズ、ローター周速10m/sにて湿式粉砕を行った。ミル内を5回繰り返し通すことでDEP−2のスラリーを得た。このとき、ミル内をスラリーが通過するのにかかる時間は、1回当り約2分間であった。同様にして、ジルコニアビーズ径、ローター周速、粉砕時間を変更し、DEP−3、DEP−4のスラリーを得た。粒子径は、レーザー回折/散乱式粒子径分布測定装置[LA−950:堀場製作所社製]を用いて、スラリーをメタノールで希釈した後、屈折率1.500、液屈折率1.329で測定した。
DEP−1を水中に分散させ、ミル内を5時間連続して繰り返し通過させたこと以外は、製造例1と同様にしてDEP−5のスラリーを得た。乾燥した後、メタノール中に分散させて、粒子径を測定した。
PPE:600gをトルエン:6,000gに40℃で溶解させた。一方、DEP−1:150gをメタノール:500gに分散させたDEPのメタノール溶液を作製した。PPEのトルエン溶液とDEPのメタノール溶液を混合し、室温にてメタノール9,000gを加えてPPEを析出(再沈殿)させた。得られた析出物をろ過後、120℃で5時間真空乾燥し、PPE/DEP−1=4/1の混合粉体を得た。DEP−5についても同様にしてPPE/DEP−5=4/1の混合粉体を得た。一方、DEP−2、DEP−3、DEP−4については、メタノール溶液作製の際に、製造例1で得られたスラリー:500gをメタノール:150gで希釈して使用したこと以外は、DEP−1と同様にしてPPE/DEP=4/1の混合粉末を得た。
以下に、評価方法について述べる。
<荷重たわみ温度(DTUL)>
実施例及び比較例で得られた樹脂組成物ペレットを、100℃の乾燥機を用いて3時間乾燥した後、射出成形機[IS−80EPN:東芝機械社製]を用いて、射出速度200mm/秒、保圧70MPa、射出+保圧時間20秒、冷却時間20秒、金型温度120℃、溶融樹脂温度330℃に設定し、ISO 3167、多目的試験片A型の成形片を成形した。得られた成形片を切削して使用し、80×10×4の試験片を用いて、ISO 75に準拠し、フラットワイズ法、1.80MPaで荷重たわみ温度を測定した。
実施例及び比較例で得られた樹脂組成物ペレットを、乾燥機を用いて120℃で3時間乾燥した後、射出成形機[IS−80EPN:東芝機械社製]を用いて、射出速度700mm/秒、保圧60MPa、射出+保圧時間10秒、冷却時間15秒、金型温度90℃、溶融樹脂温度320℃に設定し、90×50×2.5mmの平板成形片を成形した。得られた平板成形片を目視で確認し、シルバーの有無を確認した。100枚について確認し、シルバーが見られた成形品の数を評価した。
上記で成形した90×50×2.5mmの平板成形片を用いて、落錘グラフィックインパクトテスター[東洋精機社製]を用い、23℃、50RH%の条件下で、ホルダ径φ40mm、ストライカー径12.7mm、ストライカー重量6.5kgを使用し、高さ100cmから衝撃試験を行い、全吸収エネルギー及び延性破壊した数を測定した。測定は10枚の試験片を使用し、全吸収エネルギーはその平均値を測定値とした。
実施例及び比較例で得られた樹脂組成物ペレットを、乾燥機を用いて100℃で3時間乾燥した後、射出成形機[IS−80EPN:東芝機械社製]を用いて、射出速度700mm/秒、保圧100MPa、射出+保圧時間10秒、冷却時間15秒、金型温度120℃、溶融樹脂温度320℃に設定して、127×13×1.6mmの成形片を成形した。得られた試験片を用いて、UL−94(米国アンダーライターズラボラトリー規格)に基づき、5本の試験片について、各々2回ずつ接炎し、合計10回の燃焼時間について測定し、平均燃焼時間、最大燃焼時間を評価した。
実施例及び比較例で得られた樹脂組成物ペレットを、乾燥機を用いて100℃で3時間乾燥した後、シリンダーの温度290℃、Tダイス(幅:15cm)の温度300℃に設定したスクリュー径15mmの二軸押出機[KZW15TW:テクノベル社製]を用いて、スクリュー回転数200rpm、吐出量0.8kg/hで押出しシート成形を行った。シートの厚さは約100μmであった。得られたシートを200×50mmに打ち抜き、UL−94(米国アンダーライターズラボラトリー規格)に基づき、UL−94VTM試験を行った。試験は5本の試験片について、各々2回ずつ接炎し、合計10回の燃焼時間について測定し、平均燃焼時間、最大燃焼時間を評価した。
上記のようにして得られた厚さ約100μmのシート表面外観を目視で確認した。異物がほとんど見られないものを○、異物が少し見られるものを△、異物が多数見られるものを×とした。
実施例及び比較例で得られたペレットを、耐圧2.0MPa、内容量100mLのSUS314製オートクレーブに20g入れ、サイズ縦×横×厚みが10mm×20mm×2.0mmで表面を#2000研磨した炭素鋼(材質:SS400)試験片を入れ、ペレットをさらに20g入れ、炭素鋼試験片を埋没させた。オートクレーブ内部を窒素置換した後、密閉し、320℃に設定した恒温槽に4時間、静置した。流水下にオートクレーブを取出し、室温まで冷却しオートクレーブを開放した。
溶融固化したペレット中から、炭素鋼試験片を取出し、トルエンにより炭素鋼試験片に付着した樹脂を溶解除去した。
炭素鋼試験片を風乾し、0.1mg単位まで秤量し、予め測定しておいた腐食試験前の炭素鋼試験片重量で除算し、試験前後の重量減少率を質量ppmで求めた。
押出機上流側から1番目のバレルに上流側供給口を有し、L/D(押出機のシリンダーの長さ/押出機のシリンダー径)=48(バレル数:12)の二軸押出機[ZSK−26MC:コペリオン社製(ドイツ)]を用いて、上流側供給口からダイまでを290℃に設定し、スクリュー回転数300rpm、吐出量12kg/hで、表1及び表2記載の割合(質量部)となるように、上流側供給口よりPPE、PS、SEBS、DEPを供給して溶融混練し樹脂組成物ペレットを作製した。得られた樹脂組成物の、荷重たわみ温度、シルバー、面衝撃性、難燃性、シート難燃性、シート外観、金属腐食性を評価した。物性値を組成と共に表1及び表2に併記した。
これに対して、比較例1〜5の樹脂組成物からなるペレット、成形片及びシートは、シート難燃性、耐衝撃性、外観及び金属腐食性が、実施例の樹脂組成物と比較して劣っていた。
Claims (14)
- (A)ポリフェニレンエーテル及び(B)ホスフィン酸塩類を含む難燃性樹脂組成物であって、
前記(B)成分の数平均粒子径が0.01〜5μmであり、粒子径の小さい方から25%にあたる粒子の粒子径(d25)と75%にあたる粒子の粒子径(d75)の比(d75/d25)が1.0〜2.0である、樹脂組成物。 - 前記(B)成分の最大粒子径が0.01〜20μmである、請求項1記載の難燃性樹脂組成物。
- 前記(A)成分が溶解する溶媒(p)中に(A)成分を溶解させた溶液(p−A)と、前記(B)成分を溶解しない溶媒(q)中に(B)成分を分散させた溶液(q−B)と、を混合した後、前記(A)成分を溶解しない溶媒(r)を添加することにより析出させる工程を含む方法により得られる、請求項1又は2記載の難燃性樹脂組成物(ここで、qとrは同種であっても異種であってもよい)。
- 前記(B)成分は、有機溶剤中で湿式粉砕して得られるホスフィン酸塩類である、請求項1〜3のいずれか1項記載の難燃性樹脂組成物。
- 前記(B)成分は、下記式(i)及び/又は(ii)で示されるホスフィン酸塩類である、請求項1〜4のいずれか1項記載の難燃性樹脂組成物。
- (C)エラストマーをさらに含む、請求項1〜5のいずれか1項記載の難燃性樹脂組成物。
- 前記(C)成分は、少なくとも1個の芳香族ビニル化合物を主体とする重合体ブロックと、少なくとも1個の共役ジエン化合物を主体とする重合体ブロックと、からなるブロック共重合体及び/又はその水素添加されたブロック共重合体である、請求項6記載の難燃性樹脂組成物。
- (D)安定剤をさらに含む、請求項1〜7のいずれか1項記載の難燃性樹脂組成物。
- 前記(D)成分は、ヒンダードフェノール系安定剤、リン系安定剤、イオウ系安定剤からなる群から選ばれる1種以上である、請求項8記載の難燃性樹脂組成物。
- 前記(D)成分は、ペンタエリスリトールテトラキス〔3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート〕、オクタデシル−3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオネート、N,N’−ヘキサン−1,6−ジイルビス[3−(3,5−ジ−t−ブチル−4−ヒドロキシフェニル)プロピオンアミド]、1,3,5−トリメチル−2,4,6−トリス(3,5−ジ−t−ブチル−4−ヒドロキシベンジル)ベンゼン、トリス(2,4−ジ−tert−ブチルフェニル)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{2,4−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、テトラキス〔メチレン−3−(ラウリルチオ)プロピオネート〕メタン、テトラキス〔メチレン−3−(ミリスチルチオ)プロピオネート〕メタン、テトラキス〔メチレン−3−(ステアリルチオ)プロピオネート〕メタン、4,6−ビス(オクチルチオメチル)−o−クレゾール、4,6−ビス(ステアリルチオメチル)−o−クレゾール、2,6−ジ−t−ブチル−4−{4,6−ビス(オクチルチオ)−1,3,5−トリアジン−2−イルアミノ}フェノール、4,4−チオビス(3−メチル−5−t−ブチルフェノール)よりなる群から選ばれる1種以上である、請求項8又は9記載の難燃性樹脂組成物。
- (E)(A)成分以外の熱可塑性樹脂をさらに含み、(A)成分と(E)成分の合計100質量%に対し、(A)成分1〜99質量%、(E)成分1〜99質量%である、請求項1〜10のいずれか1項記載の難燃性樹脂組成物。
- 前記(E)成分は、芳香族ビニル化合物重合体、芳香族ビニル化合物共重合体、ポリプロピレン、ポリエチレン、ポリアミド6、ポリアミド66、ポリアミド66/6、芳香族環含有ポリアミド、脂肪族環含有ポリアミド、ポリフェニレンサルファイド、液晶ポリマー、ポリエーテルエーテルケトン、ポリアリレート、ポリエーテルサルフォン、ポリサルフォンから選ばれる1種以上である、請求項11記載の難燃性樹脂組成物。
- 請求項1〜12のいずれか1項記載の難燃性樹脂組成物からなる射出成形体。
- 請求項1〜12のいずれか1項記載の難燃性樹脂組成物からなるシート。
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