CA2455841C - Flame retardant compositions - Google Patents
Flame retardant compositions Download PDFInfo
- Publication number
- CA2455841C CA2455841C CA2455841A CA2455841A CA2455841C CA 2455841 C CA2455841 C CA 2455841C CA 2455841 A CA2455841 A CA 2455841A CA 2455841 A CA2455841 A CA 2455841A CA 2455841 C CA2455841 C CA 2455841C
- Authority
- CA
- Canada
- Prior art keywords
- composition according
- bis
- flame retardant
- iii
- tert
- 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.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims abstract description 135
- 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 80
- 239000003063 flame retardant Substances 0.000 title claims abstract description 72
- -1 polypropylene Polymers 0.000 claims abstract description 207
- 150000001412 amines Chemical class 0.000 claims abstract description 75
- 229920000098 polyolefin Polymers 0.000 claims abstract description 43
- 239000004743 Polypropylene Substances 0.000 claims abstract description 25
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000005262 alkoxyamine group Chemical group 0.000 claims abstract description 24
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229920001155 polypropylene Polymers 0.000 claims abstract description 21
- 239000000758 substrate Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims description 98
- 239000000654 additive Substances 0.000 claims description 58
- 229920000642 polymer Polymers 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
- 229920001577 copolymer Polymers 0.000 claims description 52
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 46
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000001931 aliphatic group Chemical group 0.000 claims description 26
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 24
- 239000005977 Ethylene Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 230000000996 additive effect Effects 0.000 claims description 21
- 239000004698 Polyethylene Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 18
- 229920000573 polyethylene Polymers 0.000 claims description 18
- 239000003381 stabilizer Substances 0.000 claims description 18
- 229920002397 thermoplastic olefin Polymers 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 claims description 13
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 125000006309 butyl amino group Chemical group 0.000 claims description 11
- 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 claims description 10
- 239000006096 absorbing agent Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229920000620 organic polymer Polymers 0.000 claims description 9
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 239000000178 monomer Substances 0.000 claims description 8
- 230000000979 retarding effect Effects 0.000 claims description 8
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 7
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 claims description 7
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims description 6
- 150000001463 antimony compounds Chemical class 0.000 claims description 6
- OSIVCXJNIBEGCL-UHFFFAOYSA-N bis(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(OCCCCCCCC)C(C)(C)C1 OSIVCXJNIBEGCL-UHFFFAOYSA-N 0.000 claims description 6
- 239000002530 phenolic antioxidant Substances 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 6
- YUAPUIKGYCAHGM-UHFFFAOYSA-N 1,2-dibromo-3-(2,3-dibromopropoxy)propane Chemical compound BrCC(Br)COCC(Br)CBr YUAPUIKGYCAHGM-UHFFFAOYSA-N 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims 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 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- 229920001169 thermoplastic Polymers 0.000 claims description 5
- OKELZJLBUAZSCL-UHFFFAOYSA-N 1-cyclohexyloxy-2,2,6,6-tetramethyl-n-octadecylpiperidin-4-amine Chemical compound CC1(C)CC(NCCCCCCCCCCCCCCCCCC)CC(C)(C)N1OC1CCCCC1 OKELZJLBUAZSCL-UHFFFAOYSA-N 0.000 claims description 4
- KGUHWHHMNQPSRV-UHFFFAOYSA-N [1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)N(OCC(C)(C)O)C(C)(C)C1 KGUHWHHMNQPSRV-UHFFFAOYSA-N 0.000 claims 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 claims description 4
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- YVVYMSXDQGDASK-UHFFFAOYSA-N 1,2,3-tribromo-4-[2-(2,3,4-tribromophenoxy)ethoxy]benzene Chemical compound BrC1=C(Br)C(Br)=CC=C1OCCOC1=CC=C(Br)C(Br)=C1Br YVVYMSXDQGDASK-UHFFFAOYSA-N 0.000 claims description 3
- NZUPFZNVGSWLQC-UHFFFAOYSA-N 1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound BrCC(Br)CN1C(=O)N(CC(Br)CBr)C(=O)N(CC(Br)CBr)C1=O NZUPFZNVGSWLQC-UHFFFAOYSA-N 0.000 claims description 3
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 3
- JLOAPAGFWFMZLD-UHFFFAOYSA-N bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) hexanedioate Chemical compound CC1(C)CC(OC(=O)CCCCC(=O)OC2CC(C)(C)N(OC3CCCCC3)C(C)(C)C2)CC(C)(C)N1OC1CCCCC1 JLOAPAGFWFMZLD-UHFFFAOYSA-N 0.000 claims description 3
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 239000003822 epoxy resin Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 239000013008 thixotropic agent Substances 0.000 claims description 2
- 238000010348 incorporation Methods 0.000 abstract description 7
- 229910052787 antimony Inorganic materials 0.000 abstract description 4
- 230000002195 synergetic effect Effects 0.000 abstract description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 53
- 125000004432 carbon atom Chemical group C* 0.000 description 43
- 238000012360 testing method Methods 0.000 description 42
- 150000003254 radicals Chemical class 0.000 description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 31
- 229940044603 styrene Drugs 0.000 description 27
- 150000002431 hydrogen Chemical class 0.000 description 23
- 239000000835 fiber Substances 0.000 description 21
- 238000009472 formulation Methods 0.000 description 21
- 101100327795 Penaeus monodon CHH3 gene Proteins 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 14
- WMNPPTFIWBUUQT-NAWIUCTOSA-N G12 Chemical compound C1=NC(C(NC(N)=N2)=O)=C2N1[C@@H]([C@@H]1O)O[C@H](COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2COP(O)(=O)O[C@H]2[C@H]([C@@H](O[C@@H]2CO)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)N2C3=C(C(NC(N)=N3)=O)N=C2)O)[C@H]1OP(O)(=O)OC[C@H]([C@@H](O)[C@H]1O)O[C@H]1N1C(N=C(NC2=O)N)=C2N=C1 WMNPPTFIWBUUQT-NAWIUCTOSA-N 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 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
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 12
- 239000004800 polyvinyl chloride Substances 0.000 description 12
- 229920000915 polyvinyl chloride Polymers 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- 229920001684 low density polyethylene Polymers 0.000 description 10
- 239000004702 low-density polyethylene Substances 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 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 9
- 239000006260 foam Substances 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 239000008188 pellet Substances 0.000 description 9
- 239000005062 Polybutadiene Substances 0.000 description 8
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 229920005669 high impact polystyrene Polymers 0.000 description 8
- 239000004797 high-impact polystyrene Substances 0.000 description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 8
- 229920002857 polybutadiene Polymers 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 239000004700 high-density polyethylene Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- 239000004114 Ammonium polyphosphate Substances 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 6
- 229920001276 ammonium polyphosphate Polymers 0.000 description 6
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 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
- 229920001903 high density polyethylene Polymers 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- 229920000307 polymer substrate Polymers 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000010998 test method Methods 0.000 description 6
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 5
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- 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 5
- 238000002485 combustion reaction Methods 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000004611 light stabiliser Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 5
- 229910052698 phosphorus Inorganic materials 0.000 description 5
- 239000011574 phosphorus Substances 0.000 description 5
- 235000014786 phosphorus Nutrition 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- KJYSXRBJOSZLEL-UHFFFAOYSA-N (2,4-ditert-butylphenyl) 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 KJYSXRBJOSZLEL-UHFFFAOYSA-N 0.000 description 4
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- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- SWZDQOUHBYYPJD-UHFFFAOYSA-N tridodecylamine Chemical compound CCCCCCCCCCCCN(CCCCCCCCCCCC)CCCCCCCCCCCC SWZDQOUHBYYPJD-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
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- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C08L27/18—Homopolymers or copolymers or tetrafluoroethene
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31251701P | 2001-08-15 | 2001-08-15 | |
| US60/312,517 | 2001-08-15 | ||
| PCT/EP2002/008767 WO2003016388A1 (en) | 2001-08-15 | 2002-08-06 | Flame retardant compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2455841A1 CA2455841A1 (en) | 2003-02-27 |
| CA2455841C true CA2455841C (en) | 2011-01-04 |
Family
ID=23211813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2455841A Expired - Fee Related CA2455841C (en) | 2001-08-15 | 2002-08-06 | Flame retardant compositions |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20040198875A1 (https=) |
| EP (1) | EP1423465B1 (https=) |
| JP (1) | JP4389248B2 (https=) |
| AT (1) | ATE432313T1 (https=) |
| CA (1) | CA2455841C (https=) |
| DE (1) | DE60232452D1 (https=) |
| TW (1) | TWI301134B (https=) |
| WO (1) | WO2003016388A1 (https=) |
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| US7323502B2 (en) * | 2002-03-12 | 2008-01-29 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| US7595074B2 (en) * | 2002-04-05 | 2009-09-29 | University Of Massachusetts Lowell | Polymeric antioxidants |
| JP2006501340A (ja) * | 2002-10-03 | 2006-01-12 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 難燃性組成物 |
| DE10255825A1 (de) * | 2002-11-29 | 2004-06-09 | Bayer Ag | Blends mit verbesserten Eigenschaften |
| GB0304247D0 (en) * | 2003-02-25 | 2003-03-26 | British Polythene Ltd | Fire retardant film |
| JP2008507613A (ja) | 2004-07-23 | 2008-03-13 | ポルノクス コーポレーション | 抗酸化マクロモノマーおよび抗酸化ポリマー、ならびにその作製方法および使用方法 |
| EP2028228B1 (en) | 2004-10-25 | 2018-12-12 | IGM Group B.V. | Functionalized nanoparticles |
| ES2562403T3 (es) * | 2004-11-02 | 2016-03-04 | Basf Se | Proceso para la síntesis de N-alcoxiaminas |
| US20070102188A1 (en) * | 2005-11-01 | 2007-05-10 | Cable Components Group, Llc | High performance support-separators for communications cable supporting low voltage and wireless fidelity applications and providing conductive shielding for alien crosstalk |
| WO2006060800A1 (en) | 2004-12-03 | 2006-06-08 | Polnox Corporation | Synthesis of aniline and phenol-based antioxidant macromonomers and corresponding polymers |
| US7678877B2 (en) * | 2004-12-03 | 2010-03-16 | Polnox Corporation | Process for the synthesis of polyalkylphenol antioxidants |
| EP1861484A2 (en) | 2005-02-22 | 2007-12-05 | Polnox Corporation | Nitrogen and hindered phenol containing dual functional macromolecular antioxidants: synthesis , performances and applications |
| CA2606303A1 (en) | 2005-03-25 | 2006-10-05 | Polnox Corporation | Alkylated and polymeric macromolecular antioxidants and methods of making and using the same |
| US7473849B2 (en) * | 2005-04-25 | 2009-01-06 | Cable Components Group | Variable diameter conduit tubes for high performance, multi-media communication cable |
| US20060237221A1 (en) * | 2005-04-25 | 2006-10-26 | Cable Components Group, Llc. | High performance, multi-media communication cable support-separators with sphere or loop like ends for eccentric or concentric cables |
| US7473850B2 (en) * | 2005-04-25 | 2009-01-06 | Cable Components Group | High performance, multi-media cable support-separator facilitating insertion and removal of conductive media |
| US7465879B2 (en) * | 2005-04-25 | 2008-12-16 | Cable Components Group | Concentric-eccentric high performance, multi-media communications cables and cable support-separators utilizing roll-up designs |
| US7462670B2 (en) * | 2005-09-22 | 2008-12-09 | Ciba Specialty Chemicals Corporation | Scratch resistant polymer compositions |
| WO2007050985A2 (en) | 2005-10-27 | 2007-05-03 | Polnox Corporation | Macromolecular antioxidants based on stξrically hindered phenolic phosphites |
| EP1966293A1 (en) * | 2005-10-27 | 2008-09-10 | Polnox Corporation | Stabilized polyolefin compositions |
| US20070161522A1 (en) | 2005-12-02 | 2007-07-12 | Cholli Ashok L | Lubricant oil compositions |
| CA2544891A1 (en) * | 2006-04-26 | 2007-10-26 | Nova Chemicals Corporation | Pipe coating composition |
| WO2008005358A2 (en) | 2006-07-06 | 2008-01-10 | Polnox Corporation | Novel macromolecular antioxidants comprising differing antioxidant moieties: structures, methods of making and using the same |
| US7767853B2 (en) | 2006-10-20 | 2010-08-03 | Polnox Corporation | Antioxidants and methods of making and using the same |
| US20110046250A1 (en) * | 2007-07-06 | 2011-02-24 | Stowell Jeffrey K | Flame retardant composition and flexible polyurethane foam prepared therewith |
| ES2463674T3 (es) | 2009-01-19 | 2014-05-28 | Basf Se | Pigmentos negros orgánicos y su preparación |
| US20110162867A1 (en) * | 2010-01-07 | 2011-07-07 | Hanwha Chemical Corporation | Telephone cable insulation composition, and telephone cable using thereof |
| EP2826043B1 (en) | 2012-03-13 | 2019-11-06 | Cable Components Group LLC | Compositions, methods, and devices providing shielding in communications cables |
| US9511523B2 (en) | 2012-03-28 | 2016-12-06 | Sabic Global Technologies B.V. | Static-dissipative foam extrusion calibration with minimized expansion loss |
| US20150111986A1 (en) * | 2012-04-06 | 2015-04-23 | Polyone Corporation | Polyolefin intumescent phosphorous flame retardant system |
| DE102012022482A1 (de) | 2012-11-19 | 2014-05-22 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Polymerzusammensetzung mit verbesserter Langzeitstabilität, hieraus hergestellte Formteile sowie Verwendungszwecke |
| DE102013005307A1 (de) | 2013-03-25 | 2014-09-25 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von organischen Oxyimiden als Flammschutzmittel für Kunststoffe sowie flammgeschützte Kunststoffzusammensetzung und hieraus hergestelltem Formteil |
| WO2015044785A2 (en) | 2013-09-27 | 2015-04-02 | Basf Se | Polyolefin compositions for building materials |
| WO2015077635A2 (en) | 2013-11-22 | 2015-05-28 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same |
| DE102014210214A1 (de) | 2014-05-28 | 2015-12-03 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von Oxyimid-enthaltenden Copolymeren oder Polymeren als Flammschutzmittel, Stabilisatoren, Rheologiemodifikatoren für Kunststoffe, Initiatoren für Polymerisations- und Pfropfprozesse, Vernetzungs- oder Kopplungsmittel sowie solche Copolymere oder Polymere enthaltende Kunststoffformmassen |
| DE102014211276A1 (de) | 2014-06-12 | 2015-12-17 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von Hydroxybenzotriazol-Derivaten und/oder Hydroxy-Indazol-Derivaten als Flammschutzmittel für Kunststoffe sowie flammgeschützte Kunststoffformmasse |
| US20180251695A1 (en) | 2017-03-01 | 2018-09-06 | Polnox Corporation | Macromolecular Corrosion (McIn) Inhibitors: Structures, Methods Of Making And Using The Same |
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| US3671487A (en) * | 1971-05-05 | 1972-06-20 | Gen Electric | Glass reinforced polyester resins containing polytetrafluoroethylene and flame retardant additives |
| US4355126A (en) * | 1974-12-06 | 1982-10-19 | General Electric Company | Flame retardant, non-dripping compositions of polyphenylene ether and acrylonitrile-butadiene-styrene |
| DE3403975A1 (de) * | 1984-02-04 | 1985-08-14 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von abs-formmassen mit verbessertem brandverhalten |
| US4708975A (en) * | 1986-04-02 | 1987-11-24 | E. I. Du Pont De Nemours And Company | Low smoke generating, high char forming, flame retardant thermoplastic multi-block copolyesters |
| US5204473A (en) * | 1987-09-21 | 1993-04-20 | Ciba-Geigy Corporation | O-substituted N-hydroxy hindered amine stabilizers |
| US5004770A (en) * | 1988-10-19 | 1991-04-02 | Ciba-Geigy Corporation | Polymeric substrates stabilized with N-substituted hindered amines |
| US5096950A (en) * | 1988-10-19 | 1992-03-17 | Ciba-Geigy Corporation | Polyolefin compositions stabilized with NOR-substituted hindered amines |
| DE4021501A1 (de) * | 1990-07-05 | 1992-01-16 | Basf Ag | Halogenfreie, flammfest ausgeruestete abs-formmassen |
| GB9211602D0 (en) * | 1992-06-02 | 1992-07-15 | Sandoz Ltd | Improvements in or relating to organic compounds |
| FR2705679B1 (fr) * | 1993-05-24 | 1998-07-10 | Sandoz Sa | Nouvelles compositions stabilisantes des matières polymères, à base de phosphonites ou phosphites et d'un stabilisant contre l'hydrolyse. |
| US5393812A (en) * | 1993-08-31 | 1995-02-28 | Hercules Incorporated | Flame retardant, light stable composition |
| RU2087506C1 (ru) * | 1994-08-17 | 1997-08-20 | Новочеркасский государственный технический университет | Композиция для антипригарного, антиадгезионного, антикоррозионного покрытия способом гетероадагуляции |
| US5508330A (en) * | 1994-11-03 | 1996-04-16 | Ciba-Geigy Corporation | Barrier property enhancement of films and molded articles |
| US5844026A (en) * | 1997-06-30 | 1998-12-01 | Ciba Specialty Chemicals Corporation | N,N',N''-tris{2,4-bis Hydrocarbyloxy-2,2,6,6-tetra-methylpiperidin-4-yl)alkylamino!-s-triazin-6-yl}-3,3'-ethylenediiminodipropylamines, their isomers and bridged derivatives and polymer compositions stabilized therewith |
| ITMI980366A1 (it) * | 1998-02-25 | 1999-08-25 | Ciba Spec Chem Spa | Preparazione di eteri amminici stericamente impediti |
| US6309987B1 (en) * | 1998-04-20 | 2001-10-30 | Bba Nonwovens Simpsonville, Inc. | Nonwoven fabric having both UV stability and flame retardancy |
| US6403683B1 (en) * | 1998-08-28 | 2002-06-11 | Teijin Chemicals Ltd | Polycarbonate resin composition and molded article |
| US6103134A (en) * | 1998-12-31 | 2000-08-15 | Motorola, Inc. | Circuit board features with reduced parasitic capacitance and method therefor |
| US6271377B1 (en) * | 1999-02-25 | 2001-08-07 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
| JP2000309692A (ja) * | 1999-04-27 | 2000-11-07 | Toray Ind Inc | 難燃性ポリブチレンテレフタレート樹脂組成物および成形品 |
| US6737456B2 (en) * | 2001-02-27 | 2004-05-18 | Bromine Compounds Ltd. | Fire-retardant polyolefin compositions |
| KR101029863B1 (ko) * | 2001-12-21 | 2011-04-18 | 시바 홀딩 인코포레이티드 | 신규한 난연제 화합물 |
-
2002
- 2002-08-06 AT AT02794707T patent/ATE432313T1/de not_active IP Right Cessation
- 2002-08-06 WO PCT/EP2002/008767 patent/WO2003016388A1/en not_active Ceased
- 2002-08-06 JP JP2003521708A patent/JP4389248B2/ja not_active Expired - Fee Related
- 2002-08-06 CA CA2455841A patent/CA2455841C/en not_active Expired - Fee Related
- 2002-08-06 DE DE60232452T patent/DE60232452D1/de not_active Expired - Lifetime
- 2002-08-06 US US10/485,377 patent/US20040198875A1/en not_active Abandoned
- 2002-08-06 EP EP02794707A patent/EP1423465B1/en not_active Expired - Lifetime
- 2002-08-13 TW TW091118150A patent/TWI301134B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE60232452D1 (de) | 2009-07-09 |
| EP1423465B1 (en) | 2009-05-27 |
| CA2455841A1 (en) | 2003-02-27 |
| EP1423465A1 (en) | 2004-06-02 |
| US20040198875A1 (en) | 2004-10-07 |
| JP4389248B2 (ja) | 2009-12-24 |
| TWI301134B (en) | 2008-09-21 |
| JP2005500421A (ja) | 2005-01-06 |
| WO2003016388A1 (en) | 2003-02-27 |
| ATE432313T1 (de) | 2009-06-15 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20170807 |