JP4787160B2 - 難燃性組成物 - Google Patents

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Publication number

JP4787160B2

JP4787160B2 JP2006530250A JP2006530250A JP4787160B2 JP 4787160 B2 JP4787160 B2 JP 4787160B2 JP 2006530250 A JP2006530250 A JP 2006530250A JP 2006530250 A JP2006530250 A JP 2006530250A JP 4787160 B2 JP4787160 B2 JP 4787160B2

Authority

JP

Japan

Prior art keywords

group

compounds

tert

optionally substituted

bis

Prior art date

2003-10-01

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.)

Expired - Lifetime

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• 239000003063 flame retardant Substances 0.000 title claims abstract description 108
• 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 100
• 239000000203 mixture Substances 0.000 title claims abstract description 72
• 150000001875 compounds Chemical class 0.000 claims abstract description 153
• 239000000758 substrate Substances 0.000 claims abstract description 79
• 238000000034 method Methods 0.000 claims abstract description 16
• 230000000979 retarding effect Effects 0.000 claims abstract 3
• -1 phosphorus compound Chemical class 0.000 claims description 140
• 125000004432 carbon atom Chemical group C* 0.000 claims description 110
• 125000002947 alkylene group Chemical group 0.000 claims description 74
• 125000000217 alkyl group Chemical group 0.000 claims description 54
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 48
• 229920006395 saturated elastomer Polymers 0.000 claims description 48
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 40
• 125000004122 cyclic group Chemical group 0.000 claims description 29
• 125000003342 alkenyl group Chemical group 0.000 claims description 22
• 150000001412 amines Chemical class 0.000 claims description 22
• 125000006413 ring segment Chemical group 0.000 claims description 20
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 19
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 239000000654 additive Substances 0.000 claims description 11
• 229910052751 metal Inorganic materials 0.000 claims description 11
• 239000002184 metal Substances 0.000 claims description 11
• 229920000098 polyolefin Polymers 0.000 claims description 10
• 229910044991 metal oxide Inorganic materials 0.000 claims description 8
• 150000004706 metal oxides Chemical class 0.000 claims description 8
• 239000004611 light stabiliser Substances 0.000 claims description 6
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 6
• 239000006096 absorbing agent Substances 0.000 claims description 5
• 239000003963 antioxidant agent Substances 0.000 claims description 5
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 5
• 239000011574 phosphorus Substances 0.000 claims description 5
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 4
• 150000001463 antimony compounds Chemical class 0.000 claims description 4
• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 4
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 4
• 239000000975 dye Substances 0.000 claims description 3
• 229910052698 phosphorus Inorganic materials 0.000 claims description 3
• 239000000049 pigment Substances 0.000 claims description 3
• 150000002443 hydroxylamines Chemical class 0.000 claims description 2
• 150000002903 organophosphorus compounds Chemical class 0.000 claims description 2
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• 238000006467 substitution reaction Methods 0.000 claims 2
• 230000000996 additive effect Effects 0.000 claims 1
• 230000003796 beauty Effects 0.000 claims 1
• 150000002978 peroxides Chemical class 0.000 abstract description 4
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• 125000003118 aryl group Chemical group 0.000 description 41
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 39
• 229910052757 nitrogen Inorganic materials 0.000 description 39
• 229920000642 polymer Polymers 0.000 description 32
• 125000002950 monocyclic group Chemical group 0.000 description 31
• 125000001424 substituent group Chemical group 0.000 description 29
• 125000000623 heterocyclic group Chemical group 0.000 description 28
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 20
• 125000000732 arylene group Chemical group 0.000 description 19
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
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• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
• 239000005977 Ethylene Substances 0.000 description 15
• 239000004743 Polypropylene Substances 0.000 description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
• 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 14
• 125000002619 bicyclic group Chemical group 0.000 description 14
• 125000004956 cyclohexylene group Chemical group 0.000 description 14
• 150000002148 esters Chemical class 0.000 description 14
• 229910052799 carbon Inorganic materials 0.000 description 13
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 239000004952 Polyamide Substances 0.000 description 11
• 229920002647 polyamide Polymers 0.000 description 11
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• 239000005062 Polybutadiene Substances 0.000 description 10
• 239000004417 polycarbonate Substances 0.000 description 10
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 9
• 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 9
• 125000004433 nitrogen atom Chemical group N* 0.000 description 9
• 229920000877 Melamine resin Polymers 0.000 description 8
• 125000004429 atom Chemical group 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 125000005842 heteroatom Chemical group 0.000 description 8
• 229920001684 low density polyethylene Polymers 0.000 description 8
• 239000004702 low-density polyethylene Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 229910052760 oxygen Inorganic materials 0.000 description 8
• 238000003672 processing method Methods 0.000 description 8
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 8
• 150000003839 salts Chemical class 0.000 description 8
• 239000000243 solution Substances 0.000 description 8
• 125000005156 substituted alkylene group Chemical group 0.000 description 8
• 125000005717 substituted cycloalkylene group Chemical group 0.000 description 8
• 150000001721 carbon Chemical group 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
• 125000004430 oxygen atom Chemical group O* 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• 239000004800 polyvinyl chloride Substances 0.000 description 7
• 229920000915 polyvinyl chloride Polymers 0.000 description 7
• 238000012545 processing Methods 0.000 description 7
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• 239000004698 Polyethylene Substances 0.000 description 6
• 239000004721 Polyphenylene oxide Substances 0.000 description 6
• 239000004793 Polystyrene Substances 0.000 description 6
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
• 150000001408 amides Chemical class 0.000 description 6
• 239000003054 catalyst Substances 0.000 description 6
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
• 230000000694 effects Effects 0.000 description 6
• 150000002367 halogens Chemical group 0.000 description 6
• 125000001072 heteroaryl group Chemical group 0.000 description 6
• 229920001903 high density polyethylene Polymers 0.000 description 6
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 6
• FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 6
• 229920000573 polyethylene Polymers 0.000 description 6
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• 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 5
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
• 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 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
• 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 5
• 229920001971 elastomer Polymers 0.000 description 5
• 229910052736 halogen Inorganic materials 0.000 description 5
• 150000002429 hydrazines Chemical class 0.000 description 5
• 150000007857 hydrazones Chemical class 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• 229910000000 metal hydroxide Inorganic materials 0.000 description 5
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
• 125000003367 polycyclic group Chemical group 0.000 description 5
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• 125000004434 sulfur atom Chemical group 0.000 description 5
• KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 4
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
• ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
• KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
• XUQNLOIVFHUMTR-UHFFFAOYSA-N 2-[[2-hydroxy-5-nonyl-3-(1-phenylethyl)phenyl]methyl]-4-nonyl-6-(1-phenylethyl)phenol Chemical compound OC=1C(C(C)C=2C=CC=CC=2)=CC(CCCCCCCCC)=CC=1CC(C=1O)=CC(CCCCCCCCC)=CC=1C(C)C1=CC=CC=C1 XUQNLOIVFHUMTR-UHFFFAOYSA-N 0.000 description 4
• ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
• CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
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• ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
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• 125000004104 aryloxy group Chemical group 0.000 description 4
• 239000002585 base Substances 0.000 description 4
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 4
• 239000012964 benzotriazole Substances 0.000 description 4
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• QKFKIYMZKDAJOR-UHFFFAOYSA-N cyclohexyl(hexadecyl)diazene Chemical compound CCCCCCCCCCCCCCCCN=NC1CCCCC1 QKFKIYMZKDAJOR-UHFFFAOYSA-N 0.000 description 4
• UGQQAJOWXNCOPY-UHFFFAOYSA-N dechlorane plus Chemical compound C12CCC3C(C4(Cl)Cl)(Cl)C(Cl)=C(Cl)C4(Cl)C3CCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl UGQQAJOWXNCOPY-UHFFFAOYSA-N 0.000 description 4
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• FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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• ONTODYXHFBKCDK-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)-1,3,5-triazine Chemical compound CC1=CC(C)=CC=C1C1=NC=NC=N1 ONTODYXHFBKCDK-UHFFFAOYSA-N 0.000 description 3
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• DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 description 3
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