AU2005250152B2 - Flame-retardants - Google Patents
Flame-retardants Download PDFInfo
- Publication number
- AU2005250152B2 AU2005250152B2 AU2005250152A AU2005250152A AU2005250152B2 AU 2005250152 B2 AU2005250152 B2 AU 2005250152B2 AU 2005250152 A AU2005250152 A AU 2005250152A AU 2005250152 A AU2005250152 A AU 2005250152A AU 2005250152 B2 AU2005250152 B2 AU 2005250152B2
- Authority
- AU
- Australia
- Prior art keywords
- tert
- bis
- flame
- butyl
- 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.)
- Ceased
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 69
- 239000000203 mixture Substances 0.000 claims abstract description 97
- 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 37
- 239000000654 additive Substances 0.000 claims abstract description 37
- 229920000620 organic polymer Polymers 0.000 claims abstract description 18
- -1 oxyl Chemical group 0.000 claims description 199
- 150000001875 compounds Chemical class 0.000 claims description 84
- 125000000217 alkyl group Chemical group 0.000 claims description 67
- 229920000642 polymer Polymers 0.000 claims description 65
- 125000004432 carbon atom Chemical group C* 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 239000003381 stabilizer Substances 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 150000001412 amines Chemical class 0.000 claims description 41
- 125000002947 alkylene group Chemical group 0.000 claims description 36
- 125000001931 aliphatic group Chemical group 0.000 claims description 27
- 239000004952 Polyamide Substances 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 229920002647 polyamide Polymers 0.000 claims description 20
- 230000000996 additive effect Effects 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 12
- 239000000758 substrate Substances 0.000 claims description 12
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 11
- 229910052736 halogen Chemical group 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000005262 alkoxyamine group Chemical group 0.000 claims description 10
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- 229920000515 polycarbonate Polymers 0.000 claims description 10
- 239000004417 polycarbonate Substances 0.000 claims description 10
- 229920000098 polyolefin Polymers 0.000 claims description 10
- 150000002367 halogens Chemical group 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- 238000012545 processing Methods 0.000 claims description 9
- 125000006309 butyl amino group Chemical group 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004611 light stabiliser Substances 0.000 claims description 8
- 229920000570 polyether Polymers 0.000 claims description 8
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 239000000835 fiber Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 7
- 229920001169 thermoplastic Polymers 0.000 claims description 7
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004793 Polystyrene Substances 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- 239000006260 foam Substances 0.000 claims description 5
- 150000002443 hydroxylamines Chemical class 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 5
- 230000000979 retarding effect Effects 0.000 claims description 5
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 230000000052 comparative effect Effects 0.000 claims description 4
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 239000002216 antistatic agent Substances 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 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 3
- 150000001879 copper Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005647 linker group Chemical group 0.000 claims description 3
- 239000006078 metal deactivator Substances 0.000 claims description 3
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 claims description 3
- 239000002667 nucleating agent Substances 0.000 claims description 3
- 239000012744 reinforcing agent Substances 0.000 claims description 3
- AZSKHRTUXHLAHS-UHFFFAOYSA-N tris(2,4-di-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(=O)(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 AZSKHRTUXHLAHS-UHFFFAOYSA-N 0.000 claims description 3
- 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 2
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical compound ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 claims description 2
- 229910003849 O-Si Inorganic materials 0.000 claims description 2
- 229910003872 O—Si Inorganic materials 0.000 claims description 2
- 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 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims 1
- 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 1
- 229910019142 PO4 Inorganic materials 0.000 abstract description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract description 10
- 239000010452 phosphate Substances 0.000 abstract description 10
- 235000013350 formula milk Nutrition 0.000 description 78
- 239000000306 component Substances 0.000 description 54
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 52
- 229920001577 copolymer Polymers 0.000 description 45
- 150000003254 radicals Chemical class 0.000 description 38
- 150000002431 hydrogen Chemical class 0.000 description 29
- 239000002253 acid Substances 0.000 description 28
- 229940044603 styrene Drugs 0.000 description 27
- 239000004743 Polypropylene Substances 0.000 description 26
- 125000000753 cycloalkyl group Chemical group 0.000 description 26
- 229920001155 polypropylene Polymers 0.000 description 26
- 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 18
- 239000005977 Ethylene Substances 0.000 description 18
- 229940093470 ethylene Drugs 0.000 description 18
- 229920000877 Melamine resin Polymers 0.000 description 17
- 229940091868 melamine Drugs 0.000 description 17
- 229910052751 metal Inorganic materials 0.000 description 17
- 239000002184 metal Substances 0.000 description 17
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 16
- 235000021317 phosphate Nutrition 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 12
- 125000003342 alkenyl group Chemical group 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 239000004114 Ammonium polyphosphate Substances 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 10
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 10
- 229920001276 ammonium polyphosphate Polymers 0.000 description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 10
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 10
- 229920000573 polyethylene Polymers 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 9
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-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
- 239000003054 catalyst Substances 0.000 description 8
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 8
- 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 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 229920001684 low density polyethylene Polymers 0.000 description 8
- 239000004702 low-density polyethylene Substances 0.000 description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 8
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 8
- 229920006324 polyoxymethylene Polymers 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 229920002397 thermoplastic olefin Polymers 0.000 description 8
- 229920002554 vinyl polymer Polymers 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 239000012964 benzotriazole Substances 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
- 150000001993 dienes Chemical class 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 238000010348 incorporation Methods 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 7
- 229920000307 polymer substrate Polymers 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- HCUOEKSZWPGJIM-IYNMRSRQSA-N (e,2z)-2-hydroxyimino-6-methoxy-4-methyl-5-nitrohex-3-enamide Chemical compound COCC([N+]([O-])=O)\C(C)=C\C(=N\O)\C(N)=O HCUOEKSZWPGJIM-IYNMRSRQSA-N 0.000 description 6
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- 101100162200 Aspergillus parasiticus (strain ATCC 56775 / NRRL 5862 / SRRC 143 / SU-1) aflD gene Proteins 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 229920000388 Polyphosphate Polymers 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
- 125000001589 carboacyl group Chemical group 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- 230000000875 corresponding effect Effects 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
- 239000004700 high-density polyethylene Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 239000011574 phosphorus Substances 0.000 description 6
- 239000001205 polyphosphate Substances 0.000 description 6
- 235000011176 polyphosphates Nutrition 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 229920001519 homopolymer Polymers 0.000 description 5
- 239000011777 magnesium Substances 0.000 description 5
- 229910052752 metalloid Inorganic materials 0.000 description 5
- 229940063557 methacrylate Drugs 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 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
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 4
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 4
- 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 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
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- 229920002396 Polyurea Polymers 0.000 description 4
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 4
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- 229920000768 polyamine Polymers 0.000 description 1
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- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
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- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000006233 propoxy propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
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- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
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- 229930003799 tocopherol Natural products 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
- ZZMPGNVAROSUSZ-UHFFFAOYSA-N triazanium;1,3,5-triazine-2,4,6-triamine;phosphate Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O.NC1=NC(N)=NC(N)=N1 ZZMPGNVAROSUSZ-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 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
- 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
- JZZBTMVTLBHJHL-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphate Chemical compound ClCC(Cl)COP(=O)(OCC(Cl)CCl)OCC(Cl)CCl JZZBTMVTLBHJHL-UHFFFAOYSA-N 0.000 description 1
- 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
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- 239000004711 α-olefin Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/527—Cyclic esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L21/00—Compositions of unspecified rubbers
Landscapes
- 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)
- Artificial Filaments (AREA)
- Nonwoven Fabrics (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Glass Compositions (AREA)
- Fireproofing Substances (AREA)
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| EP04102308.6 | 2004-05-26 | ||
| EP04102308 | 2004-05-26 | ||
| PCT/EP2005/052268 WO2005118697A1 (en) | 2004-05-26 | 2005-05-18 | Flame-retardants |
Publications (2)
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| AU2005250152A1 AU2005250152A1 (en) | 2005-12-15 |
| AU2005250152B2 true AU2005250152B2 (en) | 2011-04-21 |
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| AU2005250152A Ceased AU2005250152B2 (en) | 2004-05-26 | 2005-05-18 | Flame-retardants |
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| EP (1) | EP1749051B1 (enExample) |
| JP (1) | JP5062479B2 (enExample) |
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| AT (1) | ATE449128T1 (enExample) |
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| BR (1) | BRPI0511525A (enExample) |
| CA (1) | CA2565160C (enExample) |
| DE (1) | DE602005017763D1 (enExample) |
| MY (1) | MY145367A (enExample) |
| TW (1) | TWI385242B (enExample) |
| WO (1) | WO2005118697A1 (enExample) |
| ZA (1) | ZA200609088B (enExample) |
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| US8034870B2 (en) * | 2003-12-17 | 2011-10-11 | Sabic Innovative Plastics Ip B.V. | Flame-retardant polyester composition |
| US8188172B2 (en) * | 2003-12-17 | 2012-05-29 | Sabic Innovative Plastics Ip B.V. | Polyester compositions, method of manufacture, and uses thereof |
| WO2006024621A1 (en) * | 2004-09-03 | 2006-03-09 | Ciba Specialty Chemicals Holding Inc. | In-can stabilizers |
| KR101150816B1 (ko) * | 2008-07-03 | 2012-06-13 | 제일모직주식회사 | 난연 및 충격 개선제, 그 제조방법 및 이를 포함하는 열가소성 수지 조성물 |
| US8138244B2 (en) * | 2008-12-30 | 2012-03-20 | Sabic Innovative Plastics Ip B.V. | Reinforced polyester compositions, method of manufacture, and articles thereof |
| US7829614B2 (en) * | 2008-12-30 | 2010-11-09 | Sabic Innovative Plastics Ip B.V. | Reinforced polyester compositions, methods of manufacture, and articles thereof |
| CN102471533B (zh) * | 2009-07-06 | 2014-07-02 | 巴斯夫欧洲公司 | 苯基膦酸盐阻燃剂组合物 |
| CN102762653B (zh) | 2009-12-31 | 2015-11-25 | 陶氏环球技术有限责任公司 | 用于电线和电缆应用的无卤素阻燃热塑性组合物 |
| US8716378B2 (en) | 2010-06-29 | 2014-05-06 | Sabic Innovative Plastics Ip B.V. | Flame resistant polyester compositions, method of manufacture, and articles thereof |
| US8686072B2 (en) | 2010-06-29 | 2014-04-01 | Sabic Innovative Plastics Ip B.V. | Flame resistant polyester compositions, method of manufacture, and articles therof |
| US8987357B2 (en) * | 2011-05-27 | 2015-03-24 | Basf Se | Thermoplastic molding composition |
| EP2825589B1 (en) | 2012-03-16 | 2020-05-06 | Basf Se | Nor-hals compounds as flame retardants |
| US10227482B2 (en) | 2012-12-20 | 2019-03-12 | Byk Usa Inc. | Flame retardant polymer compositions |
| CN103061126A (zh) * | 2012-12-28 | 2013-04-24 | 苏州市华智顾纺织有限公司 | 一种阻燃粘胶纤维织物的制作方法 |
| IN2013MU01165A (enExample) * | 2013-03-26 | 2015-04-24 | Dorf Ketal Chemicals India Private Ltd | |
| BR112016006528B1 (pt) | 2013-09-27 | 2021-07-27 | Basf Se | Artigo extrudado compreendendo uma composição de poliolefina |
| TWI685524B (zh) | 2013-12-17 | 2020-02-21 | 美商畢克美國股份有限公司 | 預先脫層之層狀材料 |
| EP2947115B1 (de) * | 2014-05-22 | 2019-04-17 | Basf Se | Halogenfreie Flammschutzmischungen für Polyolefinschaumstoffe |
| DE102014218811A1 (de) * | 2014-09-18 | 2016-03-24 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von phosphorhaltigen organischen Oxyimiden als Flammschutzmittel, Radikalgeneratoren und/oder als Stabilisatoren für Kunststoffe, flammgeschützte Kunststoffzusammensetzung, Verfahren zu deren Herstellung sowie Formteile, Lacke und Beschichtungen |
| US20190010308A1 (en) | 2015-07-20 | 2019-01-10 | Basf Se | Flame Retardant Polyolefin Articles |
| JP7233157B2 (ja) * | 2016-08-31 | 2023-03-06 | 住友化学株式会社 | 非水電解液二次電池用セパレータ |
| KR20190091472A (ko) | 2016-12-22 | 2019-08-06 | 디에스엠 아이피 어셋츠 비.브이. | 개선된 열- 및 전기-저항성 열가소성 수지 조성물 |
| JP2023549936A (ja) | 2020-11-19 | 2023-11-29 | ビーエーエスエフ ソシエタス・ヨーロピア | 難燃性粉体組成物及びこの組成物から得られた３ｄ印刷物体 |
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- 2005-05-18 CN CN2005800171856A patent/CN1961035B/zh not_active Expired - Fee Related
- 2005-05-18 EP EP05749523A patent/EP1749051B1/en not_active Expired - Lifetime
- 2005-05-18 JP JP2007513911A patent/JP5062479B2/ja not_active Expired - Fee Related
- 2005-05-18 WO PCT/EP2005/052268 patent/WO2005118697A1/en not_active Ceased
- 2005-05-18 AU AU2005250152A patent/AU2005250152B2/en not_active Ceased
- 2005-05-18 DE DE602005017763T patent/DE602005017763D1/de not_active Expired - Lifetime
- 2005-05-18 BR BRPI0511525-6A patent/BRPI0511525A/pt not_active IP Right Cessation
- 2005-05-18 CA CA2565160A patent/CA2565160C/en not_active Expired - Fee Related
- 2005-05-18 AT AT05749523T patent/ATE449128T1/de not_active IP Right Cessation
- 2005-05-18 KR KR1020067024005A patent/KR101141610B1/ko not_active Expired - Fee Related
- 2005-05-18 US US11/596,731 patent/US7786199B2/en not_active Expired - Fee Related
- 2005-05-19 MY MYPI20052288A patent/MY145367A/en unknown
- 2005-05-24 TW TW094116884A patent/TWI385242B/zh not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| CA2565160A1 (en) | 2005-12-15 |
| KR20070030785A (ko) | 2007-03-16 |
| BRPI0511525A (pt) | 2007-12-26 |
| WO2005118697A9 (en) | 2006-03-09 |
| KR101141610B1 (ko) | 2012-05-22 |
| MY145367A (en) | 2012-01-31 |
| CA2565160C (en) | 2013-02-12 |
| JP2008500416A (ja) | 2008-01-10 |
| EP1749051A1 (en) | 2007-02-07 |
| DE602005017763D1 (de) | 2009-12-31 |
| US7786199B2 (en) | 2010-08-31 |
| EP1749051B1 (en) | 2009-11-18 |
| TW200609334A (en) | 2006-03-16 |
| ATE449128T1 (de) | 2009-12-15 |
| US20080269383A1 (en) | 2008-10-30 |
| AU2005250152A1 (en) | 2005-12-15 |
| CN1961035A (zh) | 2007-05-09 |
| JP5062479B2 (ja) | 2012-10-31 |
| ZA200609088B (en) | 2008-08-27 |
| TWI385242B (zh) | 2013-02-11 |
| CN1961035B (zh) | 2010-11-03 |
| WO2005118697A1 (en) | 2005-12-15 |
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