ES2343147T3 - Derivados de pirimidinas como retardantes de llama. - Google Patents

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Publication number

ES2343147T3

ES2343147T3 ES07728405T ES07728405T ES2343147T3 ES 2343147 T3 ES2343147 T3 ES 2343147T3 ES 07728405 T ES07728405 T ES 07728405T ES 07728405 T ES07728405 T ES 07728405T ES 2343147 T3 ES2343147 T3 ES 2343147T3

Authority

ES

Spain

Prior art keywords

alkyl

aryl

alkenyl

group

aralkyl

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.)

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• 239000003063 flame retardant Substances 0.000 title claims abstract description 81
• 239000000203 mixture Substances 0.000 claims abstract description 49
• 229920000620 organic polymer Polymers 0.000 claims abstract description 45
• 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 abstract description 39
• 238000000034 method Methods 0.000 claims abstract description 29
• -1 aralkylene Chemical group 0.000 claims description 145
• 150000001875 compounds Chemical class 0.000 claims description 57
• 125000003118 aryl group Chemical group 0.000 claims description 52
• 125000000217 alkyl group Chemical group 0.000 claims description 47
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 44
• 239000002253 acid Substances 0.000 claims description 41
• 229910052799 carbon Inorganic materials 0.000 claims description 39
• 229920000642 polymer Polymers 0.000 claims description 38
• 125000003342 alkenyl group Chemical group 0.000 claims description 36
• 239000004952 Polyamide Substances 0.000 claims description 27
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
• 229920002647 polyamide Polymers 0.000 claims description 27
• 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 27
• 150000003839 salts Chemical class 0.000 claims description 24
• 125000004104 aryloxy group Chemical group 0.000 claims description 23
• 239000000654 additive Substances 0.000 claims description 21
• 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 229920000877 Melamine resin Polymers 0.000 claims description 18
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
• 125000002947 alkylene group Chemical group 0.000 claims description 16
• 239000003381 stabilizer Substances 0.000 claims description 14
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 13
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 13
• 229910052698 phosphorus Inorganic materials 0.000 claims description 13
• 239000011574 phosphorus Substances 0.000 claims description 13
• 229920000728 polyester Polymers 0.000 claims description 13
• 239000003054 catalyst Substances 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 230000000996 additive effect Effects 0.000 claims description 10
• 239000004417 polycarbonate Substances 0.000 claims description 10
• 101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 9
• 125000004122 cyclic group Chemical group 0.000 claims description 9
• 239000000945 filler Substances 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 125000000304 alkynyl group Chemical group 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000003844 furanonyl 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
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 7
• 239000003963 antioxidant agent Substances 0.000 claims description 6
• 239000012744 reinforcing agent Substances 0.000 claims description 6
• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 5
• 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
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 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
• 239000003995 emulsifying agent Substances 0.000 claims description 5
• 150000002443 hydroxylamines Chemical class 0.000 claims description 5
• JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 5
• 239000004611 light stabiliser Substances 0.000 claims description 5
• 239000000314 lubricant Substances 0.000 claims description 5
• 239000002667 nucleating agent Substances 0.000 claims description 5
• 230000003287 optical effect Effects 0.000 claims description 5
• 150000002978 peroxides Chemical class 0.000 claims description 5
• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 5
• 239000000049 pigment Substances 0.000 claims description 5
• 239000004014 plasticizer Substances 0.000 claims description 5
• 238000000518 rheometry Methods 0.000 claims description 5
• 229910052717 sulfur Inorganic materials 0.000 claims description 5
• 150000001450 anions Chemical class 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 4
• 239000006078 metal deactivator Substances 0.000 claims description 4
• 229920000515 polycarbonate Polymers 0.000 claims description 4
• 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 claims description 3
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
• 239000004202 carbamide Substances 0.000 claims description 3
• 238000010348 incorporation Methods 0.000 claims description 3
• 239000012796 inorganic flame retardant Substances 0.000 claims description 3
• 150000003014 phosphoric acid esters Chemical class 0.000 claims description 3
• BISHACNKZIBDFM-UHFFFAOYSA-N 5-amino-1h-pyrimidine-2,4-dione Chemical compound NC1=CNC(=O)NC1=O BISHACNKZIBDFM-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 150000007522 mineralic acids Chemical class 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 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 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
• 230000001066 destructive effect Effects 0.000 claims 1
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract description 4
• 230000000979 retarding effect Effects 0.000 abstract description 3
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 58
• 229920001577 copolymer Polymers 0.000 description 40
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 28
• 150000002148 esters Chemical class 0.000 description 19
• 239000005977 Ethylene Substances 0.000 description 17
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 15
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
• 150000003254 radicals Chemical class 0.000 description 13
• 239000000178 monomer Substances 0.000 description 11
• 229920002857 polybutadiene Polymers 0.000 description 11
• 239000005062 Polybutadiene Substances 0.000 description 10
• 229910052751 metal Inorganic materials 0.000 description 10
• 239000002184 metal Substances 0.000 description 10
• 239000004743 Polypropylene Substances 0.000 description 9
• ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 9
• 229920002292 Nylon 6 Polymers 0.000 description 8
• 239000004698 Polyethylene Substances 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 239000007859 condensation product Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
• 229920001707 polybutylene terephthalate Polymers 0.000 description 8
• 229920000573 polyethylene Polymers 0.000 description 8
• 229920002302 Nylon 6,6 Polymers 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 239000000460 chlorine Substances 0.000 description 7
• KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
• 229920006324 polyoxymethylene Polymers 0.000 description 6
• 239000004814 polyurethane Substances 0.000 description 6
• 238000012545 processing Methods 0.000 description 6
• 239000000047 product Substances 0.000 description 6
• 229920001169 thermoplastic Polymers 0.000 description 6
• 239000004416 thermosoftening plastic Substances 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
• 229910019142 PO4 Inorganic materials 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 150000008064 anhydrides Chemical class 0.000 description 5
• 229910052801 chlorine Inorganic materials 0.000 description 5
• 150000001993 dienes Chemical class 0.000 description 5
• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
• 229920001903 high density polyethylene Polymers 0.000 description 5
• 239000004700 high-density polyethylene Substances 0.000 description 5
• WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
• 229920001684 low density polyethylene Polymers 0.000 description 5
• 239000004702 low-density polyethylene Substances 0.000 description 5
• 150000002739 metals Chemical class 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
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 5
• 229920001155 polypropylene Polymers 0.000 description 5
• 235000013772 propylene glycol Nutrition 0.000 description 5
• 239000011732 tocopherol Substances 0.000 description 5
• 229920002554 vinyl polymer Polymers 0.000 description 5
• 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
• 229920000089 Cyclic olefin copolymer Polymers 0.000 description 4
• 239000004721 Polyphenylene oxide Substances 0.000 description 4
• 239000007983 Tris buffer Substances 0.000 description 4
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
• WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
• 125000005250 alkyl acrylate group Chemical group 0.000 description 4
• 229910052782 aluminium Inorganic materials 0.000 description 4
• 235000006708 antioxidants Nutrition 0.000 description 4
• 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
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
• VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 4
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• 238000009472 formulation Methods 0.000 description 4
• XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
• 229920001519 homopolymer Polymers 0.000 description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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• ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 3
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• YZEZMSPGIPTEBA-UHFFFAOYSA-N 2-n-(4,6-diamino-1,3,5-triazin-2-yl)-1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(NC=2N=C(N)N=C(N)N=2)=N1 YZEZMSPGIPTEBA-UHFFFAOYSA-N 0.000 description 3
• RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
• CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 3
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• 235000019826 ammonium polyphosphate Nutrition 0.000 description 3
• 125000000732 arylene group Chemical group 0.000 description 3
• TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
• FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 3
• 229910052794 bromium Inorganic materials 0.000 description 3
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• UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 3
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• 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 3
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• 229910052725 zinc Inorganic materials 0.000 description 3
• 239000011701 zinc Chemical group 0.000 description 3
• GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
• ZQMPWXFHAUDENN-UHFFFAOYSA-N 1,2-bis[(2-methylphenyl)amino]ethane Natural products CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 2
• YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
• 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
• BUGAMLAPDQMYNZ-UHFFFAOYSA-N 1-(2,4,4-trimethylpentan-2-yl)-10h-phenothiazine Chemical class S1C2=CC=CC=C2NC2=C1C=CC=C2C(C)(C)CC(C)(C)C BUGAMLAPDQMYNZ-UHFFFAOYSA-N 0.000 description 2
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