KR20090009799A - 난연제로서 피리미딘의 유도체 - Google Patents

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Publication number

KR20090009799A

KR20090009799A KR1020087024687A KR20087024687A KR20090009799A KR 20090009799 A KR20090009799 A KR 20090009799A KR 1020087024687 A KR1020087024687 A KR 1020087024687A KR 20087024687 A KR20087024687 A KR 20087024687A KR 20090009799 A KR20090009799 A KR 20090009799A

Authority

KR

South Korea

Prior art keywords

alkyl

aryl

alkenyl

group

substituted

Prior art date

2006-05-02

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.)

Ceased

Links

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• 239000003063 flame retardant Substances 0.000 title claims abstract description 80
• 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 32
• 150000003230 pyrimidines Chemical class 0.000 title description 4
• 229920000620 organic polymer Polymers 0.000 claims abstract description 57
• 239000000203 mixture Substances 0.000 claims abstract description 53
• 238000000034 method Methods 0.000 claims abstract description 30
• 230000000979 retarding effect Effects 0.000 claims abstract description 15
• -1 aralkylene Chemical group 0.000 claims description 151
• 150000001875 compounds Chemical class 0.000 claims description 56
• 125000000217 alkyl group Chemical group 0.000 claims description 53
• 125000003118 aryl group Chemical group 0.000 claims description 47
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 44
• 229920001577 copolymer Polymers 0.000 claims description 41
• 125000003342 alkenyl group Chemical group 0.000 claims description 39
• 229920000642 polymer Polymers 0.000 claims description 35
• 229910052799 carbon Inorganic materials 0.000 claims description 34
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 229920002647 polyamide Polymers 0.000 claims description 24
• 150000003839 salts Chemical class 0.000 claims description 24
• 239000004952 Polyamide Substances 0.000 claims description 23
• 125000004104 aryloxy group Chemical group 0.000 claims description 23
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 20
• 239000000654 additive Substances 0.000 claims description 20
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 20
• 229920000877 Melamine resin Polymers 0.000 claims description 18
• 125000003545 alkoxy group Chemical group 0.000 claims description 18
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical group NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 18
• 125000002947 alkylene group Chemical group 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 15
• 229910052698 phosphorus Inorganic materials 0.000 claims description 15
• 239000011574 phosphorus Substances 0.000 claims description 15
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 13
• 239000003381 stabilizer Substances 0.000 claims description 13
• 229920000728 polyester Polymers 0.000 claims description 12
• 239000003054 catalyst Substances 0.000 claims description 10
• 239000000945 filler Substances 0.000 claims description 10
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 239000004417 polycarbonate Substances 0.000 claims description 10
• 239000012744 reinforcing agent Substances 0.000 claims description 10
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 9
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 229910019142 PO4 Inorganic materials 0.000 claims description 7
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000002541 furyl group Chemical group 0.000 claims description 7
• 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 7
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 6
• 150000007513 acids Chemical class 0.000 claims description 6
• 239000003963 antioxidant agent Substances 0.000 claims description 6
• LNDZXOWGUAIUBG-UHFFFAOYSA-N 6-aminouracil Chemical compound NC1=CC(=O)NC(=O)N1 LNDZXOWGUAIUBG-UHFFFAOYSA-N 0.000 claims description 5
• 239000004604 Blowing Agent Substances 0.000 claims description 5
• 239000006096 absorbing agent Substances 0.000 claims description 5
• 125000005262 alkoxyamine group Chemical group 0.000 claims description 5
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
• 239000002216 antistatic agent Substances 0.000 claims description 5
• 239000003995 emulsifying agent Substances 0.000 claims description 5
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 5
• 239000012796 inorganic flame retardant Substances 0.000 claims description 5
• 239000000314 lubricant Substances 0.000 claims description 5
• 239000006078 metal deactivator Substances 0.000 claims description 5
• 239000002667 nucleating agent Substances 0.000 claims description 5
• 230000003287 optical effect Effects 0.000 claims description 5
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 5
• 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 5
• 239000000049 pigment Substances 0.000 claims description 5
• 239000004014 plasticizer Substances 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• BISHACNKZIBDFM-UHFFFAOYSA-N 5-amino-1h-pyrimidine-2,4-dione Chemical compound NC1=CNC(=O)NC1=O BISHACNKZIBDFM-UHFFFAOYSA-N 0.000 claims description 4
• 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 claims description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
• 230000000996 additive effect Effects 0.000 claims description 4
• 150000001450 anions Chemical class 0.000 claims description 4
• 239000003623 enhancer Substances 0.000 claims description 4
• 150000002443 hydroxylamines Chemical class 0.000 claims description 4
• 239000004611 light stabiliser Substances 0.000 claims description 4
• 150000007522 mineralic acids Chemical class 0.000 claims description 4
• 239000010452 phosphate Substances 0.000 claims description 4
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 4
• 150000003014 phosphoric acid esters Chemical class 0.000 claims description 4
• 229920000515 polycarbonate Polymers 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• VFGRNTYELNYSKJ-UHFFFAOYSA-N 6-amino-1,3-dimethylpyrimidine-2,4-dione Chemical compound CN1C(N)=CC(=O)N(C)C1=O VFGRNTYELNYSKJ-UHFFFAOYSA-N 0.000 claims description 3
• 229910020366 ClO 4 Inorganic materials 0.000 claims description 3
• BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 3
• 239000004202 carbamide Substances 0.000 claims description 3
• 238000010348 incorporation Methods 0.000 claims description 3
• CWGBFIRHYJNILV-UHFFFAOYSA-N (1,4-diphenyl-1,2,4-triazol-4-ium-3-yl)-phenylazanide Chemical compound C=1C=CC=CC=1[N-]C1=NN(C=2C=CC=CC=2)C=[N+]1C1=CC=CC=C1 CWGBFIRHYJNILV-UHFFFAOYSA-N 0.000 claims description 2
• 230000003078 antioxidant effect Effects 0.000 claims description 2
• HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 claims 1
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 2
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 59
• 229910052757 nitrogen Inorganic materials 0.000 description 29
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
• 150000002148 esters Chemical class 0.000 description 18
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
• 239000005977 Ethylene Substances 0.000 description 15
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
• 150000003254 radicals Chemical class 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
• 239000007859 condensation product Chemical class 0.000 description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
• 229920002857 polybutadiene Polymers 0.000 description 11
• 239000005062 Polybutadiene Substances 0.000 description 10
• 239000000460 chlorine Substances 0.000 description 10
• ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 10
• 239000004743 Polypropylene Substances 0.000 description 9
• 239000000178 monomer Substances 0.000 description 9
• 229920002292 Nylon 6 Polymers 0.000 description 8
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 229920001684 low density polyethylene Polymers 0.000 description 8
• 239000004702 low-density polyethylene Substances 0.000 description 8
• 229910052751 metal Inorganic materials 0.000 description 8
• 239000002184 metal Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 229920002302 Nylon 6,6 Polymers 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 7
• 239000004700 high-density polyethylene Substances 0.000 description 7
• 229920001707 polybutylene terephthalate Polymers 0.000 description 7
• 229920006324 polyoxymethylene Polymers 0.000 description 7
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
• 229920001903 high density polyethylene Polymers 0.000 description 6
• QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
• 229920001169 thermoplastic Polymers 0.000 description 6
• 239000004416 thermosoftening plastic Substances 0.000 description 6
• 229920002554 vinyl polymer Polymers 0.000 description 6
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 5
• 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 5
• 239000004721 Polyphenylene oxide Substances 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
• SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 5
• 229940117969 neopentyl glycol Drugs 0.000 description 5
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• 238000006116 polymerization reaction Methods 0.000 description 5
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