JP5448426B2 - ジオルガニルホスフィン酸およびカルボン酸の混合塩 - Google Patents
ジオルガニルホスフィン酸およびカルボン酸の混合塩 Download PDFInfo
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- JP5448426B2 JP5448426B2 JP2008299205A JP2008299205A JP5448426B2 JP 5448426 B2 JP5448426 B2 JP 5448426B2 JP 2008299205 A JP2008299205 A JP 2008299205A JP 2008299205 A JP2008299205 A JP 2008299205A JP 5448426 B2 JP5448426 B2 JP 5448426B2
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- Prior art keywords
- acid
- flame retardant
- carboxylic acid
- mixed salt
- aluminum
- 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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- 239000002253 acid Substances 0.000 title claims abstract description 62
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims description 74
- 150000003839 salts Chemical class 0.000 title claims description 74
- 229920000642 polymer Polymers 0.000 claims abstract description 99
- 239000003063 flame retardant 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 89
- 239000000203 mixture Substances 0.000 claims abstract description 68
- -1 carboxylic acid anion Chemical class 0.000 claims abstract description 46
- 150000001768 cations Chemical class 0.000 claims abstract description 42
- 239000000654 additive Substances 0.000 claims abstract description 15
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 239000000945 filler Substances 0.000 claims abstract description 10
- 238000000465 moulding Methods 0.000 claims abstract description 10
- 239000000835 fiber Substances 0.000 claims abstract description 5
- 150000001450 anions Chemical class 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 29
- XSAOTYCWGCRGCP-UHFFFAOYSA-K aluminum;diethylphosphinate Chemical compound [Al+3].CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC XSAOTYCWGCRGCP-UHFFFAOYSA-K 0.000 claims description 26
- 239000012778 molding material Substances 0.000 claims description 20
- 229910052782 aluminium Inorganic materials 0.000 claims description 18
- 150000001735 carboxylic acids Chemical class 0.000 claims description 17
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 17
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- 230000007704 transition Effects 0.000 claims description 15
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 14
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052725 zinc Inorganic materials 0.000 claims description 12
- 239000011701 zinc Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 10
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 10
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- KTLIMPGQZDZPSB-UHFFFAOYSA-M diethylphosphinate Chemical compound CCP([O-])(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-M 0.000 claims description 10
- 230000000996 additive effect Effects 0.000 claims description 9
- 229920000728 polyester Polymers 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- BFPVXOYPQMBHDJ-UHFFFAOYSA-H dialuminum;terephthalate Chemical compound [Al+3].[Al+3].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1.[O-]C(=O)C1=CC=C(C([O-])=O)C=C1.[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 BFPVXOYPQMBHDJ-UHFFFAOYSA-H 0.000 claims description 6
- 229910001593 boehmite Inorganic materials 0.000 claims description 5
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 5
- KTLIMPGQZDZPSB-UHFFFAOYSA-N diethylphosphinic acid Chemical compound CCP(O)(=O)CC KTLIMPGQZDZPSB-UHFFFAOYSA-N 0.000 claims description 5
- FYIBGDKNYYMMAG-UHFFFAOYSA-N ethane-1,2-diol;terephthalic acid Chemical compound OCCO.OC(=O)C1=CC=C(C(O)=O)C=C1 FYIBGDKNYYMMAG-UHFFFAOYSA-N 0.000 claims description 5
- 229910001679 gibbsite Inorganic materials 0.000 claims description 5
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 5
- 229960001545 hydrotalcite Drugs 0.000 claims description 5
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 5
- 230000002787 reinforcement Effects 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 239000004408 titanium dioxide Substances 0.000 claims description 5
- KRYKVDUDEQTXQC-UHFFFAOYSA-H dialuminum;benzene-1,3-dicarboxylate Chemical compound [Al+3].[Al+3].[O-]C(=O)C1=CC=CC(C([O-])=O)=C1.[O-]C(=O)C1=CC=CC(C([O-])=O)=C1.[O-]C(=O)C1=CC=CC(C([O-])=O)=C1 KRYKVDUDEQTXQC-UHFFFAOYSA-H 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- 229920002959 polymer blend Polymers 0.000 claims description 4
- 239000002023 wood Substances 0.000 claims description 4
- 150000003752 zinc compounds Chemical class 0.000 claims description 4
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 3
- INZLXIUOICFWDW-UHFFFAOYSA-N bis(hydroxymethyl)phosphinic acid Chemical compound OCP(O)(=O)CO INZLXIUOICFWDW-UHFFFAOYSA-N 0.000 claims description 3
- SPWAXFLJYHRRJL-UHFFFAOYSA-N butyl(ethyl)phosphinic acid Chemical compound CCCCP(O)(=O)CC SPWAXFLJYHRRJL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 239000003623 enhancer Substances 0.000 claims description 3
- NXHKQBCTZHECQF-UHFFFAOYSA-N ethyl(methyl)phosphinic acid Chemical compound CCP(C)(O)=O NXHKQBCTZHECQF-UHFFFAOYSA-N 0.000 claims description 3
- LYYXRDZATAMURV-UHFFFAOYSA-N ethylphosphonous acid Chemical compound CCP(O)O LYYXRDZATAMURV-UHFFFAOYSA-N 0.000 claims description 3
- 238000005187 foaming Methods 0.000 claims description 3
- 238000005470 impregnation Methods 0.000 claims description 3
- 239000004922 lacquer Substances 0.000 claims description 3
- PMVVRSKJCGEFIY-UHFFFAOYSA-N methylphosphonous acid Chemical compound CP(O)O PMVVRSKJCGEFIY-UHFFFAOYSA-N 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- BXZAHARWAYSGTO-UHFFFAOYSA-K [Al+3].CCP([O-])=O.CCP([O-])=O.CCP([O-])=O Chemical compound [Al+3].CCP([O-])=O.CCP([O-])=O.CCP([O-])=O BXZAHARWAYSGTO-UHFFFAOYSA-K 0.000 claims description 2
- WVLAZEHCUADXTN-UHFFFAOYSA-K aluminum butyl(ethyl)phosphinate Chemical compound [Al+3].CCCCP([O-])(=O)CC.CCCCP([O-])(=O)CC.CCCCP([O-])(=O)CC WVLAZEHCUADXTN-UHFFFAOYSA-K 0.000 claims description 2
- 229910001377 aluminum hypophosphite Inorganic materials 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- FGYBPGJIUUUVTL-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;zinc Chemical compound [Zn].OC(=O)C1=CC=CC(C(O)=O)=C1 FGYBPGJIUUUVTL-UHFFFAOYSA-N 0.000 claims description 2
- 229910001382 calcium hypophosphite Inorganic materials 0.000 claims description 2
- 229940064002 calcium hypophosphite Drugs 0.000 claims description 2
- OZVCIJIOEZNZFL-UHFFFAOYSA-H dialuminum;phthalate Chemical compound [Al+3].[Al+3].[O-]C(=O)C1=CC=CC=C1C([O-])=O.[O-]C(=O)C1=CC=CC=C1C([O-])=O.[O-]C(=O)C1=CC=CC=C1C([O-])=O OZVCIJIOEZNZFL-UHFFFAOYSA-H 0.000 claims description 2
- KSHDLNQYVGBYHZ-UHFFFAOYSA-N dibutylphosphinic acid Chemical compound CCCCP(O)(=O)CCCC KSHDLNQYVGBYHZ-UHFFFAOYSA-N 0.000 claims description 2
- LILJQKZGAFPWHU-UHFFFAOYSA-K dizinc diethylphosphinate terephthalate Chemical compound C(C)P([O-])(=O)CC.C(C1=CC=C(C(=O)[O-])C=C1)(=O)[O-].[Zn+2].[Zn+2] LILJQKZGAFPWHU-UHFFFAOYSA-K 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052732 germanium Inorganic materials 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 150000002505 iron Chemical class 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- SEQVSYFEKVIYCP-UHFFFAOYSA-L magnesium hypophosphite Chemical compound [Mg+2].[O-]P=O.[O-]P=O SEQVSYFEKVIYCP-UHFFFAOYSA-L 0.000 claims description 2
- 229910001381 magnesium hypophosphite Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000344 soap Substances 0.000 claims description 2
- 229910052712 strontium Inorganic materials 0.000 claims description 2
- UYISKGVFPMWFJV-UHFFFAOYSA-N terephthalic acid;zinc Chemical compound [Zn].OC(=O)C1=CC=C(C(O)=O)C=C1 UYISKGVFPMWFJV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- CNALVHVMBXLLIY-IUCAKERBSA-N tert-butyl n-[(3s,5s)-5-methylpiperidin-3-yl]carbamate Chemical compound C[C@@H]1CNC[C@@H](NC(=O)OC(C)(C)C)C1 CNALVHVMBXLLIY-IUCAKERBSA-N 0.000 claims description 2
- 229910052718 tin Inorganic materials 0.000 claims description 2
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims description 2
- GTOWTBKGCUDSNY-UHFFFAOYSA-K tris[[ethyl(methyl)phosphoryl]oxy]alumane Chemical compound [Al+3].CCP(C)([O-])=O.CCP(C)([O-])=O.CCP(C)([O-])=O GTOWTBKGCUDSNY-UHFFFAOYSA-K 0.000 claims description 2
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 claims description 2
- UXDZLUCNRYCZCG-UHFFFAOYSA-L zinc;phthalate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1C([O-])=O UXDZLUCNRYCZCG-UHFFFAOYSA-L 0.000 claims description 2
- 229910052726 zirconium Inorganic materials 0.000 claims description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- PPYGOLMZUNREJY-UHFFFAOYSA-K aluminum;bis(hydroxymethyl)phosphinate Chemical compound [Al+3].OCP([O-])(=O)CO.OCP([O-])(=O)CO.OCP([O-])(=O)CO PPYGOLMZUNREJY-UHFFFAOYSA-K 0.000 claims 1
- DRYHXHUXMMIMPH-UHFFFAOYSA-L calcium;diethylphosphinate Chemical compound [Ca+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DRYHXHUXMMIMPH-UHFFFAOYSA-L 0.000 claims 1
- PTLIZOFGXLGHSY-UHFFFAOYSA-N dibutylphosphane Chemical compound CCCCPCCCC PTLIZOFGXLGHSY-UHFFFAOYSA-N 0.000 claims 1
- UUAARYXSOYDWSN-UHFFFAOYSA-K diethylphosphinate iron(3+) Chemical compound [Fe+3].CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC UUAARYXSOYDWSN-UHFFFAOYSA-K 0.000 claims 1
- HFVKYLPSHXAMME-UHFFFAOYSA-J diethylphosphinate;titanium(4+) Chemical compound [Ti+4].CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC HFVKYLPSHXAMME-UHFFFAOYSA-J 0.000 claims 1
- 125000005442 diisocyanate group Chemical group 0.000 claims 1
- HHYXZVYUIJDJAH-UHFFFAOYSA-L magnesium;diethylphosphinate Chemical compound [Mg+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC HHYXZVYUIJDJAH-UHFFFAOYSA-L 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 239000000463 material Substances 0.000 abstract description 4
- 150000001734 carboxylic acid salts Chemical class 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 230000000855 fungicidal effect Effects 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract description 2
- 239000004009 herbicide Substances 0.000 abstract description 2
- 230000001681 protective effect Effects 0.000 abstract 2
- 238000005728 strengthening Methods 0.000 abstract 2
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- 230000010534 mechanism of action Effects 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 230000008635 plant growth Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 33
- 229920001577 copolymer Polymers 0.000 description 29
- 239000000047 product Substances 0.000 description 26
- 229920001778 nylon Polymers 0.000 description 21
- 239000004677 Nylon Substances 0.000 description 16
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 11
- 238000013329 compounding Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229920000877 Melamine resin Polymers 0.000 description 10
- 239000004952 Polyamide Substances 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- 229920001707 polybutylene terephthalate Polymers 0.000 description 10
- 239000004417 polycarbonate Substances 0.000 description 10
- 229920002292 Nylon 6 Polymers 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- 238000000634 powder X-ray diffraction Methods 0.000 description 9
- 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
- FEZROVYTCNUGNX-UHFFFAOYSA-K aluminum;diethylphosphinate;terephthalate Chemical compound [Al+3].CCP([O-])(=O)CC.[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 FEZROVYTCNUGNX-UHFFFAOYSA-K 0.000 description 8
- 238000001746 injection moulding Methods 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 229920002302 Nylon 6,6 Polymers 0.000 description 7
- 229920000388 Polyphosphate Polymers 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229920001684 low density polyethylene Polymers 0.000 description 7
- 239000004702 low-density polyethylene Substances 0.000 description 7
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 239000001205 polyphosphate Substances 0.000 description 7
- 235000011176 polyphosphates Nutrition 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 6
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- 235000014692 zinc oxide Nutrition 0.000 description 6
- 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 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 5
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- 241000219112 Cucumis Species 0.000 description 4
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920006055 Durethan® Polymers 0.000 description 4
- 239000002174 Styrene-butadiene Substances 0.000 description 4
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920006380 polyphenylene oxide Polymers 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
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- 239000012994 photoredox catalyst Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 239000006069 physical mixture Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001627 poly(4-methyl styrene) Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920003055 poly(ester-imide) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920003251 poly(α-methylstyrene) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920006123 polyhexamethylene isophthalamide Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000005518 polymer electrolyte Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920005996 polystyrene-poly(ethylene-butylene)-polystyrene Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 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
- 238000001556 precipitation Methods 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229910000275 saponite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- ZTUXEFFFLOVXQE-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O.CCCCCCCCCCCCCC(O)=O ZTUXEFFFLOVXQE-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 239000003017 thermal stabilizer Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Chemical class 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 1
- 230000008467 tissue growth Effects 0.000 description 1
- SLKRGHBFYYVSLH-UHFFFAOYSA-K tris(dibutylphosphoryloxy)alumane Chemical compound [Al+3].CCCCP([O-])(=O)CCCC.CCCCP([O-])(=O)CCCC.CCCCP([O-])(=O)CCCC SLKRGHBFYYVSLH-UHFFFAOYSA-K 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
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 0.000 description 1
- MQWLIFWNJWLDCI-UHFFFAOYSA-L zinc;carbonate;hydrate Chemical compound O.[Zn+2].[O-]C([O-])=O MQWLIFWNJWLDCI-UHFFFAOYSA-L 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
- BHTBHKFULNTCHQ-UHFFFAOYSA-H zinc;tin(4+);hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Zn+2].[Sn+4] BHTBHKFULNTCHQ-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/14—Monocyclic dicarboxylic acids
- C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
- C07C63/26—1,4 - Benzenedicarboxylic acid
- C07C63/28—Salts thereof
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007057210.9 | 2007-11-26 | ||
| DE102007057210A DE102007057210A1 (de) | 2007-11-26 | 2007-11-26 | Mischsalze von Diorganylphosphinsäuren und Carbonsäuren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009149862A JP2009149862A (ja) | 2009-07-09 |
| JP2009149862A5 JP2009149862A5 (enExample) | 2012-01-19 |
| JP5448426B2 true JP5448426B2 (ja) | 2014-03-19 |
Family
ID=40377605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008299205A Expired - Fee Related JP5448426B2 (ja) | 2007-11-26 | 2008-11-25 | ジオルガニルホスフィン酸およびカルボン酸の混合塩 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8221658B2 (enExample) |
| EP (1) | EP2062904B1 (enExample) |
| JP (1) | JP5448426B2 (enExample) |
| AT (1) | ATE471330T1 (enExample) |
| DE (2) | DE102007057210A1 (enExample) |
| ES (1) | ES2343921T3 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100025643A1 (en) * | 2008-07-31 | 2010-02-04 | Clariant International Ltd. | Flame-retardant mixture for thermoplastic polymers, and flame-retardant polymers |
| CN102149762B (zh) * | 2008-08-27 | 2013-07-31 | 巴斯夫欧洲公司 | 具有聚合物分散剂的阻燃组合物 |
| US8604105B2 (en) | 2010-09-03 | 2013-12-10 | Eastman Chemical Company | Flame retardant copolyester compositions |
| DE102011112080A1 (de) | 2011-09-03 | 2013-03-07 | Entex Rust & Mitschke Gmbh | Einarbeitung von Additiven und Füllstoffen in einem Planetwalzenextruder oder einem Planetwalzenextruderabschnitt |
| JP6508942B2 (ja) | 2011-12-22 | 2019-05-08 | スリーエム イノベイティブ プロパティズ カンパニー | メルトブロープロセス、低収縮性メルトブローポリマー繊維及び繊維構造体、並びにメルトブロー可能なポリマー組成物 |
| WO2015087886A1 (ja) * | 2013-12-13 | 2015-06-18 | 旭化成ケミカルズ株式会社 | ポリアミド組成物、成形品、ｌｅｄ用反射板、及び熱による反射率の低下を抑制する方法 |
| DE102015223432A1 (de) * | 2015-11-26 | 2017-06-01 | Clariant International Ltd | Polymere Flammschutzmittelmischungen |
| SE539376C2 (en) * | 2016-02-03 | 2017-08-29 | Deflamo Ab | A Polymer composition comprising a fire suppressant |
| SE539377C2 (en) * | 2016-02-24 | 2017-08-29 | Deflamo Ab | A process for manufacturing of fire suppressing crystals |
| CN113480803B (zh) * | 2021-07-13 | 2024-01-12 | 韩山师范学院 | 一种阻燃聚烯烃复合材料及其制备方法和应用 |
| JP2024514058A (ja) * | 2021-10-18 | 2024-03-28 | エルジー・ケム・リミテッド | リン系難燃剤、及びこれを含む熱可塑性樹脂組成物 |
| WO2024251716A1 (en) * | 2023-06-08 | 2024-12-12 | Loramendi, S.Coop. | Sand core and sand core making method |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3001938A (en) * | 1958-04-01 | 1961-09-26 | Exxon Research Engineering Co | Lubricants containing salts of organic-substituted phosphorus - containing acids |
| US4038249A (en) * | 1973-05-14 | 1977-07-26 | Ciba-Geigy Corporation | Metal salts of benzoyloxybenzoates and compositions stabilized therewith |
| DE19614424A1 (de) * | 1996-04-12 | 1997-10-16 | Hoechst Ag | Synergistische Flammschutzmittel-Kombination für Polymere |
| DE19652009A1 (de) * | 1996-12-13 | 1998-06-18 | Hoechst Ag | Verfahren zur Herstellung von Aluminiumsalzen von Phosphinsäuren |
| EP0919560B1 (de) * | 1997-11-28 | 2004-02-25 | Clariant GmbH | Verfahren zur Herstellung von Metallsalzen von Aryl-alkylphosphinsäuren |
| DE10359815A1 (de) * | 2003-12-19 | 2005-07-28 | Clariant Gmbh | Verfahren zur Herstellung von Dialkylphosphinsäure-Salzen |
-
2007
- 2007-11-26 DE DE102007057210A patent/DE102007057210A1/de not_active Withdrawn
-
2008
- 2008-11-20 AT AT08020200T patent/ATE471330T1/de active
- 2008-11-20 ES ES08020200T patent/ES2343921T3/es active Active
- 2008-11-20 DE DE502008000794T patent/DE502008000794D1/de active Active
- 2008-11-20 EP EP08020200A patent/EP2062904B1/de not_active Not-in-force
- 2008-11-21 US US12/313,523 patent/US8221658B2/en not_active Expired - Fee Related
- 2008-11-25 JP JP2008299205A patent/JP5448426B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES2343921T3 (es) | 2010-08-12 |
| US20090137707A1 (en) | 2009-05-28 |
| DE502008000794D1 (de) | 2010-07-29 |
| ATE471330T1 (de) | 2010-07-15 |
| EP2062904B1 (de) | 2010-06-16 |
| EP2062904A1 (de) | 2009-05-27 |
| US8221658B2 (en) | 2012-07-17 |
| JP2009149862A (ja) | 2009-07-09 |
| DE102007057210A1 (de) | 2009-05-28 |
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