JP2015218164A - スピロビスホスファイト系化合物及びその使用 - Google Patents
スピロビスホスファイト系化合物及びその使用 Download PDFInfo
- Publication number
- JP2015218164A JP2015218164A JP2014237672A JP2014237672A JP2015218164A JP 2015218164 A JP2015218164 A JP 2015218164A JP 2014237672 A JP2014237672 A JP 2014237672A JP 2014237672 A JP2014237672 A JP 2014237672A JP 2015218164 A JP2015218164 A JP 2015218164A
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- Prior art keywords
- polymer
- compound
- antioxidant
- phosphite
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000003963 antioxidant agent Substances 0.000 claims abstract description 83
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 61
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 15
- 239000011574 phosphorus Substances 0.000 claims abstract description 15
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 75
- -1 3,3 ′, 5,5′-tetra-tert-butyl-1,1′-biphenyl-2,2′-diyl Chemical group 0.000 claims description 54
- 229920000642 polymer Polymers 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 13
- 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 claims description 10
- 239000004743 Polypropylene Substances 0.000 claims description 9
- 229920001155 polypropylene Polymers 0.000 claims description 9
- 229920001169 thermoplastic Polymers 0.000 claims description 9
- 239000004698 Polyethylene Substances 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 8
- 229920000573 polyethylene Polymers 0.000 claims description 8
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229920000058 polyacrylate Polymers 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 229920006324 polyoxymethylene Polymers 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 4
- 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 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 3
- 235000013539 calcium stearate Nutrition 0.000 claims description 3
- 239000008116 calcium stearate Substances 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- RGASRBUYZODJTG-UHFFFAOYSA-N 1,1-bis(2,4-ditert-butylphenyl)-2,2-bis(hydroxymethyl)propane-1,3-diol dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C=CC(=C1)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1)C(C)(C)C)C(C)(C)C RGASRBUYZODJTG-UHFFFAOYSA-N 0.000 claims description 2
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 claims description 2
- 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 2
- KRAKFYVQCQAZOW-UHFFFAOYSA-N 2-butyl-2-ethylpropane-1,3-diol;(2,4,6-tritert-butylphenyl) dihydrogen phosphite Chemical compound CCCCC(CC)(CO)CO.CC(C)(C)C1=CC(C(C)(C)C)=C(OP(O)O)C(C(C)(C)C)=C1 KRAKFYVQCQAZOW-UHFFFAOYSA-N 0.000 claims description 2
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 claims description 2
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 claims description 2
- 239000005995 Aluminium silicate Substances 0.000 claims description 2
- 229920000106 Liquid crystal polymer Polymers 0.000 claims description 2
- 239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims description 2
- FDBMBOYIVUGUSL-UHFFFAOYSA-N OP(O)OP(O)O.C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1C(C)(C)C)C)C(C)(C)C Chemical compound OP(O)OP(O)O.C(C)(C)(C)C1=C(C(=CC(=C1)C)C(C)(C)C)C(O)(C(CO)(CO)CO)C1=C(C=C(C=C1C(C)(C)C)C)C(C)(C)C FDBMBOYIVUGUSL-UHFFFAOYSA-N 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- 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 2
- 229930182556 Polyacetal Natural products 0.000 claims description 2
- 239000004642 Polyimide Substances 0.000 claims description 2
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 2
- 239000004793 Polystyrene Substances 0.000 claims description 2
- 229920002396 Polyurea Polymers 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000006096 absorbing agent Substances 0.000 claims description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 2
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- 235000012211 aluminium silicate Nutrition 0.000 claims description 2
- 239000002216 antistatic agent Substances 0.000 claims description 2
- SXXILWLQSQDLDL-UHFFFAOYSA-N bis(8-methylnonyl) phenyl phosphite Chemical compound CC(C)CCCCCCCOP(OCCCCCCCC(C)C)OC1=CC=CC=C1 SXXILWLQSQDLDL-UHFFFAOYSA-N 0.000 claims description 2
- 235000019282 butylated hydroxyanisole Nutrition 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 239000006229 carbon black Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000004088 foaming agent Substances 0.000 claims description 2
- 239000003365 glass fiber Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000012760 heat stabilizer Substances 0.000 claims description 2
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004611 light stabiliser Substances 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 239000006078 metal deactivator Substances 0.000 claims description 2
- 239000010445 mica Substances 0.000 claims description 2
- 229910052618 mica group Inorganic materials 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 2
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 claims description 2
- 229920002492 poly(sulfone) Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 claims description 2
- 239000004926 polymethyl methacrylate Substances 0.000 claims description 2
- 229920001955 polyphenylene ether Polymers 0.000 claims description 2
- 229920006380 polyphenylene oxide Polymers 0.000 claims description 2
- 229920002223 polystyrene Polymers 0.000 claims description 2
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 2
- 239000004800 polyvinyl chloride Substances 0.000 claims description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 2
- 239000000454 talc Substances 0.000 claims description 2
- 229910052623 talc Inorganic materials 0.000 claims description 2
- 229920002725 thermoplastic elastomer Polymers 0.000 claims description 2
- 229920002397 thermoplastic olefin Polymers 0.000 claims description 2
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims 1
- ZUNGGJHBMLMRFJ-UHFFFAOYSA-O ethoxy-hydroxy-oxophosphanium Chemical compound CCO[P+](O)=O ZUNGGJHBMLMRFJ-UHFFFAOYSA-O 0.000 claims 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 claims 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract description 9
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 23
- 239000002861 polymer material Substances 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 14
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- 238000012545 processing Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000008188 pellet Substances 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000001125 extrusion Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000013329 compounding Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 230000004075 alteration Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000004262 Ethyl gallate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 230000003064 anti-oxidating effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004042 decolorization Methods 0.000 description 3
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000013112 stability test Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 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 description 2
- 0 CC(C)(c1ccccc1)c(cc(*)cc1)c1OP(OC1)OCC11COP(Oc2c(C(C)(C)c3ccccc3)cc(*)cc2)OC1 Chemical compound CC(C)(c1ccccc1)c(cc(*)cc1)c1OP(OC1)OCC11COP(Oc2c(C(C)(C)c3ccccc3)cc(*)cc2)OC1 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000032683 aging Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000005453 pelletization Methods 0.000 description 2
- 239000002530 phenolic antioxidant Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 2
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- ONHZKWDILKBQLS-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(C(C)(C)C=2C=CC=CC=2)=C1 ONHZKWDILKBQLS-UHFFFAOYSA-N 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 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 description 1
- MKRAVXYVVMSWIR-UHFFFAOYSA-N CC(C)(C)CC(C)(C)c(cc1)cc(C(C)(C)c2ccccc2)c1OP(OC1)OCC11COP(Oc2ccc(C(C)(C)CC(C)(C)C)cc2C(C)(C)c2ccccc2)OC1 Chemical compound CC(C)(C)CC(C)(C)c(cc1)cc(C(C)(C)c2ccccc2)c1OP(OC1)OCC11COP(Oc2ccc(C(C)(C)CC(C)(C)C)cc2C(C)(C)c2ccccc2)OC1 MKRAVXYVVMSWIR-UHFFFAOYSA-N 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- 241000285023 Formosa Species 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000000418 atomic force spectrum Methods 0.000 description 1
- ZEFSGHVBJCEKAZ-UHFFFAOYSA-N bis(2,4-ditert-butyl-6-methylphenyl) ethyl phosphite Chemical compound CC=1C=C(C(C)(C)C)C=C(C(C)(C)C)C=1OP(OCC)OC1=C(C)C=C(C(C)(C)C)C=C1C(C)(C)C ZEFSGHVBJCEKAZ-UHFFFAOYSA-N 0.000 description 1
- DSSYKIVIOFKYAU-UHFFFAOYSA-N camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical group C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
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Abstract
Description
(作製実施例1:本発明の化学式VIIの化合物(以下、「化合物VII」)の作製)
氷浴中の1L4つ首丸底フラスコに、34.1gのペンタエリトリトール及び70gのトルエンを連続してかき混ぜながら追加した。20℃の冷浴の下、71.3gの三塩化リンを漏斗を用いて30分間、丸底フラスコに滴下しながら追加した。得られた混合物は、反応させるためにさらに30分間かき混ぜられた。冷浴を取り除き、30分間、混合物を真空の下周囲の温度にまでもっていった。そして、51.1gのトリエチルアミン及び140gのトルエンの混合物が丸底フラスコに追加され、得られた混合物を80℃にまで温めた。161.9gの2−クミル−4−tert−オクタフェノ−ル(Schenectady International社)及び140gのトルエンの混合物が60分間、丸底フラスコに漏斗を用いながら滴下して追加された。追加が終わった後、反応させるために、混合物は60分間、80℃に保たれた。薄膜クロマトグラフィー(TLC)を通じて反応が終了したと決定された後、混合物は濾過され、濾過ケークは70gのトルエンで洗浄された。濾過は3gのトリエチルアミンと組み合わされて追加され、100gの水で2度抽出された。有機層は、収集され、真空の下で濃縮された。濃縮物は、化合物VIIを得るためにトルエン及びメタノールの混合溶液において再結晶され、白色結晶、収率82%を得た。
1HNMR(400MHz,CDCl3):0.75(s,18H,−C(CH3)2CH2C(CH3)3),1.39(s,12H,−C(CH3)2CH2C(CH3)3),1.66(s,12H,−C(CH3)2ArH),1.75(s,4H,−C(CH3)2CH2C(CH3)3),2.55−2.60(t,2H,−CCH2OP−),2.84−2.88(d,2H,−CCH2OP−),3.47−3.50(d,2H,−CCH2OP−),3.96−4.02(t,2H,−CCH2OP−),6.85−6.87(d,2H,−OArH−),7.11−7.16(td,8H,−C(CH3)2ArH,−OArH−),7.20−7.24(t,4H,−C(CH3)2ArH),7.54(s,2H,−OArH−)
13CNMR(CDCl3/TMS):30.02,30.62,31.79,31.87,32.40,36.08,38.33,42.31,57.08,61.63,61.86,76.69,77.00,77.32,117.19,117.36,124.93,125.03,125.36,125.71,128.06,137.84,143.96,148.27,148.34,151.92
元素分析:算出:C%=72.83,H%=8.39,O%=11.41,P%=7.37;検出:C%=72.90,H%=8.59,O%=11.65,P%=7.10
高解像度質量スペクトル(電子衝撃)(HRMS(EI)):算出:840.46;検出:840.60
下記の通常の抗酸化化合物(比較例化合物IからVI)及び本発明の化学式VIIの化合物(化合物VII)が、7日間、周囲温度で80%の湿度に曝された。暴露前後のTGA温度(つまり、1重量%の損失温度)及び化合物の酸価は、測定され、下記の表1及び表2において表にされた。
比較例化合物I:Deox 68(Chitec Tchnology社)、化学式Iによって示された化合物
比較例化合物II:Deox 604(Chitec Tchnology社)、化学式IIによって示された化合物
比較例化合物III:米国特許第4983657号明細書に従って作成され、化学式IIIによって示された化合物
比較例化合物IV:ADK STAB(登録商標) PEP-36(Adeka社)、化学式IVによって示された化合物
比較例化合物V:Doverphos(登録商標)S-9228PC(Dover Chemical社)、化学式Vによって示された化合物
比較例化合物VI:Irgafos(登録商標) 12(BASF社)、化学式VIによって示された化合物
化合物VII:本発明の化学式VIIの化合物
比較例の化合物IからVI及び本発明の化合物VIIはそれぞれ、280℃で、2時間熱せられ、それらの色の変化を観察し、以下の表3に作表した。
ポリプロピレン(MFI=0.3)(TAIRIPRO B1101,Formosa Chemicals & Fiber社)100質量部を挽いて粉にし、0.05質量部のステアリン酸カルシウム及び0.05質量部のペンタエリストリトールテトラキス(3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピネート)(Deox 10という名称のフェノール性抗酸化剤、Chitec Technology社)に均等に混合した。そして混合物は、ポリプロピレン化合物を形成するために0.15質量部の比較例の化合物I、V若しくはVI又は化合物VIIに加えられた。ポリプロピレン化合物は、スクリュ速度220rpm、280℃の低せん断力形状の条件で、5から10℃の水浴冷却システムを備えるCoperionツインスクリュー押出機を用いて調合され、ペレット化された。
ポリエチレン(MFI=3)(NA 112-27、USI Corporation社)100質量部を挽いて粉にし、0.05質量部のペンタエリストリトールテトラキス(3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピネート)(Deox 10という名称のフェノール性抗酸化剤、Chitec Technology社)に均等に混合した。そして混合物は、ポリエチレン化合物を形成するために0.15質量部の比較例の化合物I、V若しくはVI又は化合物VIIに加えられた。ポリエチレン化合物は、スクリュ速度220rpm、220℃の低せん断力形状の条件で、5から10℃の水浴冷却システムを備えるCoperionツインスクリュー押出機を用いて調合され、ペレット化された。
ポリブチレンテレフタレート(ガラスファイバー及び難燃剤含有CCP PBT4130-104D、Chang Chun Plastics社)100質量部を挽いて粉にし、ポリブチレンテレフタレート化合物を形成するために0.2質量部の比較例の化合物I、V若しくはVI又は化合物VIIに加えられた。得られた組成物は、スクリュ速度250rpm、300℃の下、出力40kg/時間の条件で、Coperionツインスクリュー押出機を用いて調合され、ペレット化された。
本願は、2014年5月14日に出願された台湾特許出願第103116958号明細書の利益を主張し、その主題を参考をもってここに組み込む。
Claims (16)
- Rが、C7−C9のアルキル基である請求項1に記載の化合物。
- 請求項1から3のいずれか1項に記載のスピロビスホスファイト系化合物を含む抗酸化剤。
- ヒンダードフェノール抗酸化成分、リン系抗酸化成分、硫黄系抗酸化成分、アミン系抗酸化成分及びこれらの組み合わせからなる群から選択される抗酸化成分をさらに含む請求項4に記載の抗酸化剤。
- 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、オクタデシル−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピネート、1,3,5−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、1,1,3−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、4,4’−イソプロピリデン−ジフェノール(ビスフェノールA)、ブチル化ヒドロキシアニソール(BHA)、N,N’−ヘキサメチレン−ビス−3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)プロピナイミド及びこれらの組み合わせからなる群から選択されるヒンダードフェノール抗酸化成分をさらに含む請求項4又は5に記載の抗酸化剤。
- トリス−(2,4−ジ−t−ブチルフェニル)ホスファイト、ジステアリルペンタエリトリトールジホスファイト、トリスノニルフェニルホスファイト、フェニルジイソデシルホスファイト、ジフェニルイソシルホスファイト、トリフェニルホスファイト、トリラウリルホスファイト、アルキル(C12−C15)ビスフェノールAホスファイト、アルキル(C10)ビスフェノールAホスファイト、ビス−(2,4−ジ−t−ブチルフェニル)ペンタエリトリトールジホスファイト、2−ブチル−2−エチル−1,3−プロパンジオール2,4,6−トリ−t−ブチルフェノールホスファイト、ビス−(2,6−ジ−t−ブチル−4−メチルフェニル)ペンタエリトリトールジホスファイト、ビス−(2,4−ジ−t−ブチル−6−メチルフェニル)エチルホスファイト、2,2’,2’’−ニトリロトリエタノールトリス−(3,3’、5,5’−テトラ−tert−ブチル−1、1’−ビフェニル−2,2’−ジイル)−ホスファイト及びこれらの組み合わせからなる群から選択されるリン系抗酸化成分をさらに含む請求項4から6のいずれか1項に記載の抗酸化剤。
- ポリマーと、
請求項1から3のいずれか1項に記載のスピロビスホスファイト系化合物又は請求項4から7のいずれか1項に記載の抗酸化剤と、
を含むポリマー組成物。 - 前記スピロビスホスファイト系化合物又は前記抗酸化剤の量は、前記ポリマー100質量部に対して、約0.01質量部から約5質量部である請求項8に記載のポリマー組成物。
- 前記スピロビスホスファイト系化合物又は前記抗酸化剤の量は、前記ポリマー100質量部に対して、約0.05質量部から約0.5質量部である請求項8又は9に記載のポリマー組成物。
- 前記ポリマーは、ポリエステル、ポリアルキルフタレート、ポリウレタン、ポリスルホン、ポリイミド、ポリフェニレンエーテル、スチレン系ポリマー、アクリレート系ポリマー、ポリアミド、ポリアセタール、ハロゲン含有ポリマー、ポリオレフィン及びこれらの組み合わせからなる群から選択される請求項8から10のいずれか1項に記載のポリマー組成物。
- 前記ポリマーは、熱可塑性ポリマーである請求項8から11のいずれか1項に記載のポリマー組成物。
- 前記ポリマーは、ポリアミド、ポリハイドロカーボン、ポリエステル、ポリカーボネート、ポリエチレン、ポリプロピレン、ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリスチレン、ポリアクリレート、ポリ(メチルメタクリレート)、ポリ塩化ビニル、ポリフェニレンオキサイド、ポリオキシメチレン、熱可塑性ポリオレフィン、熱可塑性エラストマー、液晶ポリマー、ポリウレタン、ポリウレア、スチレン−アクリロニトリルコポリマー、スチレン−ブタジエンコポリマー、アクリロニトリル−ブタジエン−スチレンコポリマー及び上記のいずれかの組み合わせからなる群から選択される熱可塑性ポリマーである請求項8から12のいずれか1項に記載のポリマー組成物。
- 前記ポリマーは、ポリハイドロカーボン、ポリエステル及びこれらの組み合わせからなる群から選択される熱可塑性ポリマーである請求項8から13のいずれか1項に記載のポリマー組成物。
- 熱安定剤、フィラー、相溶剤、難燃剤、UV吸収剤、光安定剤、金属不活性化剤、核化剤、可塑剤、潤滑剤、乳化剤、顔料、光沢剤、帯電防止剤、発泡剤及びこれらの組み合わせからなる群から選択される添加剤をさらに含む請求項8から14のいずれか1項に記載のポリマー組成物。
- ガラスファイバー、ステアリン酸カルシウム、炭酸カルシウム、ケイ酸塩、タルク、カオリン、マイカ、硫酸バリウム、シリコンカーバイド、カーボンブラック、二酸化シリコン、水酸化アルミニウム及びこれらの組み合わせからなる群から選択されるフィラーを含み、前記フィラーの量は、前記ポリマー100質量部に対して、約0.01質量部から約50質量部である請求項8から15のいずれか1項に記載のポリマー組成物。
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EP (1) | EP2944644B1 (ja) |
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CN (1) | CN105085573A (ja) |
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CN105949243B (zh) * | 2016-05-12 | 2018-11-06 | 营口风光新材料股份有限公司 | 一种亚磷酸酯类抗氧剂9228的制备方法 |
CN108129515A (zh) * | 2017-12-05 | 2018-06-08 | 中海油天津化工研究设计院有限公司 | 一种双亚磷酸酯的合成方法 |
TWI754807B (zh) * | 2019-04-10 | 2022-02-11 | 財團法人紡織產業綜合研究所 | 聚酯光變色組成物以及聚酯光變色纖維的製備方法 |
CN110229421B (zh) * | 2019-07-02 | 2021-11-09 | 中广核俊尔(浙江)新材料有限公司 | 一种耐高温注塑聚丙烯材料及其制备方法和应用 |
CN110885130A (zh) * | 2019-12-03 | 2020-03-17 | 江西夏氏春秋环境股份有限公司 | 一种污水处理用加载微生物的生物填料及制备方法 |
CN114315904B (zh) * | 2022-01-18 | 2022-11-01 | 江苏极易新材料有限公司 | 一种双(2,4-二枯基苯基)季戊四醇二亚磷酸酯的合成方法 |
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US4463112A (en) * | 1980-02-13 | 1984-07-31 | Leistner William E | Phenylethylidene-substituted phenyl polyphosphites |
JPH0280439A (ja) * | 1988-07-25 | 1990-03-20 | Borg Warner Specialty Chem Inc | ビス(トリ‐t‐アルキルフエノキシ)ジホスフアスピロウンデカン |
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US4187212A (en) | 1975-02-20 | 1980-02-05 | Ciba-Geigy Corporation | Stabilization systems from triarylphosphites and phenols |
CA1078862A (en) | 1976-03-04 | 1980-06-03 | James F. York | Preparation of organic phosphites |
JPS56152863A (en) | 1980-04-28 | 1981-11-26 | Adeka Argus Chem Co Ltd | Synthetic resin composition |
US4318845A (en) | 1980-11-24 | 1982-03-09 | Ciba-Geigy Corporation | Alkanolamine esters of 1,1'-biphenyl-2,2'-diyl-and alkylidene-1,1'-biphenyl-2,2'-diyl-cyclic phosphites |
CS252501B1 (en) * | 1982-11-09 | 1987-09-17 | Maria Povazancova | Thermal and light-stabilized mixture on base of polypropylene |
CS269587B1 (en) | 1988-05-31 | 1990-04-11 | Humplik Antonin | Stabilizing composition for polymere materials |
US5141975A (en) * | 1991-06-07 | 1992-08-25 | General Electric Company | Thermoplastic compositions containing hydrolytically stable phosphites |
US5364895A (en) | 1993-01-20 | 1994-11-15 | Dover Chemical Corp. | Hydrolytically stable pentaerythritol diphosphites |
KR100413583B1 (ko) | 1993-08-30 | 2004-05-10 | 도버 케미칼 코포레이션 | 가수분해안정성펜타에리트리톨디포스파이트 |
US5917076A (en) * | 1998-04-16 | 1999-06-29 | General Electric Company | Process for the preparation of spiro bis-phosphites using finely ground pentaerythritol |
WO1999064506A1 (en) * | 1998-06-11 | 1999-12-16 | Teijin Limited | η-RAY STABILIZER AND THERMOPLASTIC POLYMER COMPOSITION CONTAINING THE SAME |
EP1338574A1 (en) * | 2002-02-13 | 2003-08-27 | Asahi Glass Co., Ltd. | Glass fiber and thermoplastic resin composition |
CN101326454B (zh) * | 2005-12-12 | 2010-11-03 | 柯尼卡美能达精密光学株式会社 | 偏光板的制造方法,偏光板及液晶显示装置 |
CN104403290B (zh) * | 2014-11-28 | 2016-06-22 | 上海锦湖日丽塑料有限公司 | 一种耐候性能优异的pc/abs合金及其制备方法 |
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- 2014-10-10 US US14/511,893 patent/US20150329703A1/en not_active Abandoned
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- 2014-11-12 CA CA2870410A patent/CA2870410C/en active Active
- 2014-11-19 KR KR1020140161383A patent/KR20150130896A/ko not_active Application Discontinuation
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US4463112A (en) * | 1980-02-13 | 1984-07-31 | Leistner William E | Phenylethylidene-substituted phenyl polyphosphites |
JPH0280439A (ja) * | 1988-07-25 | 1990-03-20 | Borg Warner Specialty Chem Inc | ビス(トリ‐t‐アルキルフエノキシ)ジホスフアスピロウンデカン |
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CA2870410C (en) | 2016-08-02 |
EP2944644B1 (en) | 2017-11-01 |
TW201542577A (zh) | 2015-11-16 |
KR20150130896A (ko) | 2015-11-24 |
EP2944644A1 (en) | 2015-11-18 |
US20150329703A1 (en) | 2015-11-19 |
ES2654686T3 (es) | 2018-02-14 |
TWI503326B (zh) | 2015-10-11 |
CA2870410A1 (en) | 2015-11-14 |
JP6063430B2 (ja) | 2017-01-18 |
CN105085573A (zh) | 2015-11-25 |
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