WO2014060004A1 - Procédé de production de métal-hydroxydiphényl-2' -(thio)phosphinates et de métal-diphénylène-(thio)phosphonates, compositions les contenant et leur utilisation comme agents ignifuges - Google Patents
Procédé de production de métal-hydroxydiphényl-2' -(thio)phosphinates et de métal-diphénylène-(thio)phosphonates, compositions les contenant et leur utilisation comme agents ignifuges Download PDFInfo
- Publication number
- WO2014060004A1 WO2014060004A1 PCT/EP2012/004330 EP2012004330W WO2014060004A1 WO 2014060004 A1 WO2014060004 A1 WO 2014060004A1 EP 2012004330 W EP2012004330 W EP 2012004330W WO 2014060004 A1 WO2014060004 A1 WO 2014060004A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- metal
- formula
- oxide
- composition according
- melamine
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 64
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 229910052751 metal Inorganic materials 0.000 claims abstract description 62
- 239000002184 metal Substances 0.000 claims abstract description 62
- 229920000642 polymer Polymers 0.000 claims abstract description 33
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 29
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 17
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 15
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 11
- 229910052718 tin Inorganic materials 0.000 claims abstract description 11
- 229910052802 copper Inorganic materials 0.000 claims abstract description 10
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 9
- 229920001587 Wood-plastic composite Polymers 0.000 claims abstract description 8
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 8
- 229910052796 boron Inorganic materials 0.000 claims abstract description 8
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011155 wood-plastic composite Substances 0.000 claims abstract description 8
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 5
- 239000000123 paper Substances 0.000 claims abstract description 3
- 239000004753 textile Substances 0.000 claims abstract description 3
- 239000011701 zinc Substances 0.000 claims description 75
- 239000011777 magnesium Substances 0.000 claims description 49
- -1 basic metal carbonates Chemical class 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 28
- 239000003063 flame retardant Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 21
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 21
- 229910052782 aluminium Inorganic materials 0.000 claims description 18
- 229920000877 Melamine resin Polymers 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000011575 calcium Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 15
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 14
- 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 description 13
- 229910001463 metal phosphate Inorganic materials 0.000 claims description 13
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 claims description 11
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 10
- 150000004692 metal hydroxides Chemical class 0.000 claims description 10
- 239000004417 polycarbonate Substances 0.000 claims description 10
- 238000007363 ring formation reaction Methods 0.000 claims description 10
- YTLIXUAGIGBJAF-UHFFFAOYSA-N 6-hydroxybenzo[c][2,1]benzoxaphosphinine 6-oxide Chemical compound C1=CC=C2P(O)(=O)OC3=CC=CC=C3C2=C1 YTLIXUAGIGBJAF-UHFFFAOYSA-N 0.000 claims description 9
- SCARISRKCRGDJL-UHFFFAOYSA-N O=P1OSO1 Chemical class O=P1OSO1 SCARISRKCRGDJL-UHFFFAOYSA-N 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 9
- 229920000388 Polyphosphate Polymers 0.000 claims description 9
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 9
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 9
- 229920002647 polyamide Polymers 0.000 claims description 9
- 229920002959 polymer blend Polymers 0.000 claims description 9
- 239000001205 polyphosphate Substances 0.000 claims description 9
- 235000011176 polyphosphates Nutrition 0.000 claims description 9
- 239000007921 spray Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 229910052742 iron Inorganic materials 0.000 claims description 8
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims description 7
- 150000004706 metal oxides Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- 239000004800 polyvinyl chloride Substances 0.000 claims description 7
- 229910001593 boehmite Inorganic materials 0.000 claims description 6
- 235000011180 diphosphates Nutrition 0.000 claims description 6
- FAHBNUUHRFUEAI-UHFFFAOYSA-M hydroxidooxidoaluminium Chemical compound O[Al]=O FAHBNUUHRFUEAI-UHFFFAOYSA-M 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 6
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 6
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003822 epoxy resin Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 238000005469 granulation Methods 0.000 claims description 5
- 230000003179 granulation Effects 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 5
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- 229920001169 thermoplastic Polymers 0.000 claims description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims description 5
- 239000004416 thermosoftening plastic Substances 0.000 claims description 5
- WMXBGWKUWMQWAL-UHFFFAOYSA-H trizinc 1,3,5-triazine-2,4,6-triamine diphosphate Chemical compound N1=C(N)N=C(N)N=C1N.P(=O)([O-])([O-])[O-].[Zn+2].P(=O)([O-])([O-])[O-].[Zn+2].[Zn+2] WMXBGWKUWMQWAL-UHFFFAOYSA-H 0.000 claims description 5
- 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 claims description 5
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 claims description 5
- RQSXOGGLRKMDBA-UHFFFAOYSA-N 6-hydroxy-6-sulfanylidenebenzo[c][2,1]benzoxaphosphinine Chemical compound C1=CC=C2P(O)(=S)OC3=CC=CC=C3C2=C1 RQSXOGGLRKMDBA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 4
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 4
- 241001061127 Thione Species 0.000 claims description 4
- XBKJSMNSWPBHGD-UHFFFAOYSA-B [O-]P([O-])(=O)OP(=O)([O-])[O-].N1=C(N)N=C(N)N=C1N.[Al+3].[O-]P([O-])(=O)OP(=O)([O-])[O-].[O-]P([O-])(=O)OP(=O)([O-])[O-].[Al+3].[Al+3].[Al+3] Chemical compound [O-]P([O-])(=O)OP(=O)([O-])[O-].N1=C(N)N=C(N)N=C1N.[Al+3].[O-]P([O-])(=O)OP(=O)([O-])[O-].[O-]P([O-])(=O)OP(=O)([O-])[O-].[Al+3].[Al+3].[Al+3] XBKJSMNSWPBHGD-UHFFFAOYSA-B 0.000 claims description 4
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical group [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 4
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical class [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
- 125000005402 stannate group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 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 3
- 229910001679 gibbsite Inorganic materials 0.000 claims description 3
- 239000010439 graphite Substances 0.000 claims description 3
- 229910002804 graphite Inorganic materials 0.000 claims description 3
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 3
- 229960001545 hydrotalcite Drugs 0.000 claims description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- GWLJTAJEHRYMCA-UHFFFAOYSA-N phospholane Chemical compound C1CCPC1 GWLJTAJEHRYMCA-UHFFFAOYSA-N 0.000 claims description 3
- 229920000747 poly(lactic acid) Polymers 0.000 claims description 3
- 229920000515 polycarbonate Polymers 0.000 claims description 3
- 239000004626 polylactic acid Substances 0.000 claims description 3
- 229920005862 polyol Polymers 0.000 claims description 3
- 150000003077 polyols Chemical class 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 239000004114 Ammonium polyphosphate Substances 0.000 claims description 2
- 239000004640 Melamine resin Substances 0.000 claims description 2
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- RKFMOTBTFHXWCM-UHFFFAOYSA-M [AlH2]O Chemical compound [AlH2]O RKFMOTBTFHXWCM-UHFFFAOYSA-M 0.000 claims description 2
- ZZTXLNLNVIMDIR-UHFFFAOYSA-A [O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].N1=C(N)N=C(N)N=C1N.N1=C(N)N=C(N)N=C1N.[Al+3].[O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[Al+3].[Al+3].[Al+3].[Al+3] Chemical compound [O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].N1=C(N)N=C(N)N=C1N.N1=C(N)N=C(N)N=C1N.[Al+3].[O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[O-]P([O-])(=O)OP(=O)([O-])OP(=O)([O-])[O-].[Al+3].[Al+3].[Al+3].[Al+3] ZZTXLNLNVIMDIR-UHFFFAOYSA-A 0.000 claims description 2
- UBIHIBUAEYNWRG-UHFFFAOYSA-J [O-]P([O-])(=O)OP(=O)([O-])[O-].N1=C(N)N=C(N)N=C1N.N1=C(N)N=C(N)N=C1N.[Zn+2].[Zn+2] Chemical compound [O-]P([O-])(=O)OP(=O)([O-])[O-].N1=C(N)N=C(N)N=C1N.N1=C(N)N=C(N)N=C1N.[Zn+2].[Zn+2] UBIHIBUAEYNWRG-UHFFFAOYSA-J 0.000 claims description 2
- QGAVSDVURUSLQK-UHFFFAOYSA-N ammonium heptamolybdate Chemical group N.N.N.N.N.N.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.[Mo].[Mo].[Mo].[Mo].[Mo].[Mo].[Mo] QGAVSDVURUSLQK-UHFFFAOYSA-N 0.000 claims description 2
- 235000019826 ammonium polyphosphate Nutrition 0.000 claims description 2
- 229920001276 ammonium polyphosphate Polymers 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims description 2
- VBQRUYIOTHNGOP-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinine 6-oxide Chemical compound C1=CC=C2P(=O)OC3=CC=CC=C3C2=C1 VBQRUYIOTHNGOP-UHFFFAOYSA-N 0.000 claims description 2
- LJUXFZKADKLISH-UHFFFAOYSA-N benzo[f]phosphinoline Chemical class C1=CC=C2C3=CC=CC=C3C=CC2=P1 LJUXFZKADKLISH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052599 brucite Inorganic materials 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229920001568 phenolic resin Polymers 0.000 claims description 2
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 claims description 2
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 claims description 2
- 229920000193 polymethacrylate Polymers 0.000 claims description 2
- 238000001694 spray drying Methods 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 229910021536 Zeolite Inorganic materials 0.000 claims 3
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims 3
- 239000010457 zeolite Substances 0.000 claims 3
- BISHACNKZIBDFM-UHFFFAOYSA-N 5-amino-1h-pyrimidine-2,4-dione Chemical compound NC1=CNC(=O)NC1=O BISHACNKZIBDFM-UHFFFAOYSA-N 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- 229910052728 basic metal Inorganic materials 0.000 claims 2
- 239000010452 phosphate Substances 0.000 claims 2
- 239000011135 tin Substances 0.000 claims 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 claims 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 claims 1
- VFGRNTYELNYSKJ-UHFFFAOYSA-N 6-amino-1,3-dimethylpyrimidine-2,4-dione Chemical compound CN1C(N)=CC(=O)N(C)C1=O VFGRNTYELNYSKJ-UHFFFAOYSA-N 0.000 claims 1
- PWLLPWRFJSNOAJ-UHFFFAOYSA-H [Mg++].[Mg++].[Mg++].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.Nc1nc(N)nc(N)n1 Chemical compound [Mg++].[Mg++].[Mg++].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.Nc1nc(N)nc(N)n1 PWLLPWRFJSNOAJ-UHFFFAOYSA-H 0.000 claims 1
- 229920001222 biopolymer Polymers 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-M dioxido(phenyl)phosphanium Chemical compound [O-]P(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-M 0.000 claims 1
- 239000005007 epoxy-phenolic resin Substances 0.000 claims 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 1
- 229920000058 polyacrylate Polymers 0.000 claims 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 claims 1
- CVMZFKBYOUZFCN-UHFFFAOYSA-N C1C(C=CC2=C1C1=C(P(O2)=O)C=CC=C1)=S Chemical compound C1C(C=CC2=C1C1=C(P(O2)=O)C=CC=C1)=S CVMZFKBYOUZFCN-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- GEIAQOFPUVMAGM-UHFFFAOYSA-N ZrO Inorganic materials [Zr]=O GEIAQOFPUVMAGM-UHFFFAOYSA-N 0.000 abstract description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000000725 suspension Substances 0.000 description 17
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 15
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 14
- 238000005119 centrifugation Methods 0.000 description 12
- 239000012153 distilled water Substances 0.000 description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000011787 zinc oxide Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- 229920001707 polybutylene terephthalate Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229930040373 Paraformaldehyde Natural products 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 229920002396 Polyurea Polymers 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
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- YGANSGVIUGARFR-UHFFFAOYSA-N dipotassium dioxosilane oxo(oxoalumanyloxy)alumane oxygen(2-) Chemical compound [O--].[K+].[K+].O=[Si]=O.O=[Al]O[Al]=O YGANSGVIUGARFR-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000010433 feldspar Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000001046 glycoluril group Chemical group [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000271 hectorite Inorganic materials 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229910052960 marcasite Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052627 muscovite Inorganic materials 0.000 description 1
- 125000005487 naphthalate group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 229910001682 nordstrandite Inorganic materials 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical class OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
- FUSRYQFNOAIOLF-UHFFFAOYSA-N phenylphosphonic acid;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)C1=CC=CC=C1 FUSRYQFNOAIOLF-UHFFFAOYSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000004850 phospholanes Chemical class 0.000 description 1
- 150000004857 phospholes Chemical class 0.000 description 1
- QVJYHZQHDMNONA-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1.NC1=NC(N)=NC(N)=N1 QVJYHZQHDMNONA-UHFFFAOYSA-N 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229910052615 phyllosilicate Inorganic materials 0.000 description 1
- 239000000049 pigment 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
- 239000005015 poly(hydroxybutyrate) Substances 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
- 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
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 239000004633 polyglycolic acid Chemical class 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001470 polyketone Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol 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
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229910052683 pyrite Inorganic materials 0.000 description 1
- 239000011028 pyrite Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 102220157709 rs144942998 Human genes 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- YPPQYORGOMWNMX-UHFFFAOYSA-L sodium phosphonate pentahydrate Chemical compound [Na+].[Na+].[O-]P([O-])=O YPPQYORGOMWNMX-UHFFFAOYSA-L 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VLCLHFYFMCKBRP-UHFFFAOYSA-N tricalcium;diborate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]B([O-])[O-].[O-]B([O-])[O-] VLCLHFYFMCKBRP-UHFFFAOYSA-N 0.000 description 1
- NFMWFGXCDDYTEG-UHFFFAOYSA-N trimagnesium;diborate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]B([O-])[O-].[O-]B([O-])[O-] NFMWFGXCDDYTEG-UHFFFAOYSA-N 0.000 description 1
- WUUHFRRPHJEEKV-UHFFFAOYSA-N tripotassium borate Chemical compound [K+].[K+].[K+].[O-]B([O-])[O-] WUUHFRRPHJEEKV-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- VUDJAFZYSMINQA-UHFFFAOYSA-L zinc metaphosphate Chemical compound [Zn+2].[O-]P(=O)=O.[O-]P(=O)=O VUDJAFZYSMINQA-UHFFFAOYSA-L 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
- HRSADIZPZPRZEI-UHFFFAOYSA-L zinc;diacetate;hydrate Chemical compound O.[Zn+2].CC([O-])=O.CC([O-])=O HRSADIZPZPRZEI-UHFFFAOYSA-L 0.000 description 1
- XJUNLJFOHNHSAR-UHFFFAOYSA-J zirconium(4+);dicarbonate Chemical compound [Zr+4].[O-]C([O-])=O.[O-]C([O-])=O XJUNLJFOHNHSAR-UHFFFAOYSA-J 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65744—Esters of oxyacids of phosphorus condensed with carbocyclic or heterocyclic rings or ring systems
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
- C07F9/4841—Aromatic acids or derivatives (P-C aromatic linkage)
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
-
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
Definitions
- the invention relates to a process for the preparation of metal (thio) phosphinates starting from (6H) -dibenz (c, e) (1,2) -oxaphosphorin-6-one / thione (oxide / sulfide) or from 10-hydroxy- 9,10-Dihydro-9-oxa-phosphaphenanthrene-10-oxide (on) or of 10-hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-sulfide / (thione) and
- WPC wood plastic composites
- 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (6H-dibenz [c, e] [1,2] oxaphosphorine-6-oxide) and its polymeric derivatives are indeed flame retardants in certain polyesters
- 9,10-dihydro-9-oxa-10-phosphaphenanthren-10-oxide (6H-dibenz [c, e] [1, 2] oxa-phosphorin-6 oxide) or polymeric derivatives thereof are not readily processable or metered and necessary for processing
- 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (6H-dibenz [c, e] [1,2] oxa-phosphorine-6-oxide) derivatives based on metal salts can remedy this situation.
- Salts of diorganylphosphinic acids, in particular their alkali metal and alkaline earth metal salts, and their use as flame retardants for polyesters and polyamides are known, for example, from DE 225 2258 and DE 244 7727. Mixtures of these salts with nitrogen bases and their use as effective flame retardants are described, for example, in WO 97/39053.
- Diorganylphosphinic acids especially since the Monoorganylphosphin Acid Acid, which still have a P-H bond, are expressly referred to as disadvantageous, because they because of their light
- Oxidability are unstable and thereby lose their flame retardancy over time.
- JP 2001-139586 discloses the use of the zinc and aluminum salts of 10-hydroxy-9,0-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide as flame retardants for organic polymers.
- the synthesis of these two salts takes place by double reaction starting from sodium phosphonate and metal chloride or metal sulfate.
- precipitates difficult to filter are obtained, which also have a high residual chloride content.
- the process is also not environmentally friendly because wastewater ballast must be disposed of with a high salt load.
- the starting phosphonic acid is only by oxidation with
- the zinc salt is also obtainable by reacting zinc acetate (hydrate) in ethanol and 10-hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (JP 53127484). This process is uneconomical, since the alcohol
- JP2003-306585 describes magnesium-bis-2-hydroxydiphenyl-2 phosphinate 'and the Mg-salt of 10-hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide as nucleating agents for polypropylene. A use as a flame retardant is not published.
- JP07-330963 describes the same salts as transparency improver for
- JP04-252245 describes barium bis (1'-hydroxy-2,2'-biphenylenephosphinate) in combination with inorganic fillers for use in polyolefins for improving the mechanical properties.
- JP03-223354 also describes zinc bis (1'-hydroxy-2,2'-biphenylene phosphinate) in combination with inorganic fillers for the improvement of
- EP 1 657 972 A1 discloses a reaction product which is obtained by double reaction of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (6H-dibenz [c, e] [1, 2] oxa phosphoric-6-oxide) with NaOH / H 2 O with ZnC ⁇ .
- the precipitation product thus obtained has the composition of zinc-bis-2-hydroxydiphenyl-2 '- phosphinate.
- a homologous aluminum salt is also exemplified in this document.
- This patent also discloses a combination of melamine polyphosphate and melamine cyanurate, respectively, prepared by the method described above
- Zinc phosphinate described in relation to the burning behavior of polyamide.
- step (b) optionally reacting the metal (thio) phosphinates of the formula (I) from step (a) in a cyclization reaction for the preparation of
- Mt is selected from Cu, Ca, Mg, Zn, Mn, Fe, Al, Co, Ni, Sn, TiO, Zr, ZrO, Ce, MoO, W0 2 , VO, B, Si, La, Ti, Bi or Sb;
- Mt is selected from Al, Ca, Cu, Mg, Zn or Zr.
- Particular preference is given to a process which uses metal metal oxides CaO, MgO, ZnO as starting materials and Ca (OH) 2 , Mg (OH) 2 , Zn (OH) 2 and / or Al (OH) 3 as metal hydroxides.
- ZnO and Ca (OH) 2 and Mg (OH) 2 are particularly preferred as starting materials.
- starting materials in particular basic copper carbonate, basic magnesium carbonate, basic zinc carbonate, basic zirconium carbonate and basic aluminum carbonate.
- Particularly preferred starting materials are basic magnesium carbonate (hydromagnesite) and basic zinc carbonate (hydrozincite).
- mixtures of two or more of the abovementioned compounds can also be used as starting materials.
- step (a) is preferably carried out in the aqueous phase, if appropriate in the presence of alcohols. Furthermore, step (a) is preferably carried out at a temperature of 20 to 90 ° C, more preferably at 30 to 70 ° C.
- a granulation process can be followed by step (a). This may be preferred as spray agglomeration either in the spray dryer,
- Spray granulator top spray or bottom spray, countercurrent process
- Fluidized bed granulator or in a paddle mixer or horizontal dryer, wherein the introduced water is removed until the desired residual moisture is obtained.
- the granulation can take place by spray-drying an aqueous suspension of a metal (thio) phosphinate of the formula (I) at 70-80 ° C. or alternatively as spray granulation starting from a
- Eduktmischung and spraying water onto the fluidized bed and subsequent drying can be obtained.
- the fluidized bed temperature is kept constant between 70-80 ° C, the granules dry at the same time and a free-flowing, non-dusting granules formed.
- the residual water content is approx. 0.5 - 1%.
- the preparation of metal phosphonates (III) in step (b) is preferably anhydrous by thermal cyclization of metal (thio) phosphinates (I). This can be done in a mixer or dryer, electric oven, rotary kiln or in one High-speed mixer to be performed. Particularly preferably, the cyclization is carried out in a vertical or horizontal paddle mixer.
- the cyclization is typically carried out at 130 to 270 ° C, preferably at 170 to 220 ° C and more preferably at 180 to 200 ° C.
- a flame retardant composition according to the invention has an improved flame retardancy in a variety compared to the individual components
- synergistic compositions are used. These other components may be metal-containing or metal-free.
- the present invention thus further relates to a composition
- a composition comprising (i) a metal (thio) phosphonate of the formula (III), optionally in
- synergistic components (ii-a) and (ii-b) of the composition according to the invention are shown below.
- the other metal-containing component (ii-a) other than component (i) may in particular comprise metal hydroxide, metal phosphate, metal pyrophosphate, hydrotalcite, hydrocalumite, cationic or anionic modified organoclay, stannate salt or molybdate salt, metal borate or a metal phosphinate of formula (IV) .
- R and R 2 are independently hydrogen, linear or branched CC 6 alkyl or phenyl, Mt 1 is Ca, Mg, Zn or Al and m is 2 or 3.
- component (ii-a) are melamine metal phosphates such as
- M 2 ZP 2 bis-melamine zinc diphosphate
- M 2 AP 3 bis-melamine magnesium diphosphate
- M 2 AP 3 bis-melamine aluminum triphosphate
- component (ii) are azine metal phosphates of the general formula [I],
- M is selected from Cu, Mg, Ca, Zn, Mn, Fe, Co, Ni, TiO, ZrO, VO, B, Si, Al, Sb, La, Ti, Zr, Ce, Bi or Sn,
- n 2 or 3
- x and y are independently 0 or 1
- p is an integer from 0 to 4.
- z is an integer> 5,
- hydrotalcite and hydrokalumite have, for example, the composition Mg 6 Al 2 (OH) i 6 CO 3 and Ca 1 OH 2 CO 3 .
- Organoclays are understood as meaning organophilically modified clay minerals (mainly montmorillonites) based on cation exchange, such as triethanol-tallow-ammonium-montmorillonite and triethanol-tallow-ammonium-hectorite, as described in Dr. med. G. Beyer; Conf. Fire Resistance in Plastics, 2007.
- Anionic organoclays are preferably organophil-modified hydrotalcites based on anion exchange with alkali metal roosinates, unsaturated and saturated fatty acid salts and long-chain alkyl-substituted sulfonates and sulfates.
- Metal oxides are preferably selected from diantimony trioxide, diantimony tetroxide, diantimony pentoxide, zinc oxide or mixtures thereof.
- metal phosphate metal pyrophosphates are preferred. Particularly preferred are aluminum and zinc pyrophosphate, zinc and aluminum triphosphate, aluminum and zinc metaphosphate, aluminum and zinc orthophosphate or mixtures thereof.
- the alkyl sulfate or fatty acid carboxylate-modified hydrotalcites or long-chain quaternary ammonium-modified clay minerals are particularly preferred.
- Aluminum trihydroxide ATH, gibbsite
- aluminum monohydroxide boehmite
- hydromagnesite and hydrozincite hydromagnesite and hydrozincite.
- gibbsite and boehmite the other modifications of aluminum hydroxides, namely bayerite, nordstrandite and diaspore are also mentioned.
- Zinkhydroxystannat or mixtures thereof also act as
- metal borates alkali, alkaline earth or zinc borate are preferred. Also to be mentioned are aluminum borate, barium borate, calcium borate,
- Metal phosphinates are preferably salts in which Mt is selected from Ca, Mg, Zn or Al.
- Preferred metal phosphinates are phenylphosphinate diethyl (methyl, ethyl) phosphinate, especially in combination with the aforementioned metals.
- the Mg, Ca, Zn and Al salts are particularly preferred.
- Composition includes in particular red phosphorus, oligomeric
- Phosphate esters oligomeric phosphonate esters, cyclic phosphonate esters,
- Thiopyrophosphoric acid ester melamine orthophosphate or melamine pyrophosphate, di- Melamine phosphate, melamine polyphosphate, melam (polyphosphate), and, Meiern and Diguanidinphosphat, Melaminphenylphosphinat, monomeric, oligomeric and polymeric Melaminphenylphosphonat, ammonium polyphosphate, melamine phenylphosphonate and its half ester salt, as in WO 2010/063623
- melaminebenzene phosphinate as described in WO 2010/057851, hydroxyalkyl-phosphine oxides, as described in WO 2009/034023, tetrakis-hydroxymethyl-phosphonium salts and phospholane (oxide) - or phosphole derivatives and bisphosphoramidates with piperazine as a bridge member or a phosphinate ester, the substance class of NOR-HALS compounds (non-basic aminoether hindered amine light stabilizer) and mixtures thereof.
- NOR-HALS compounds non-basic aminoether hindered amine light stabilizer
- oligomeric phosphate esters are phosphate esters of formula (VI) or formula (VII),
- y is 0 or 2.
- Particularly preferred is bis [5-ethyl-2-methyl-1,3,2-dioxaphosphorinan-5-ate) methyl] methyl phosphonate P, P ' dioxide.
- hydroxyalkyl-phosphine oxides preference is given to isobutyl-bis-hydroxymethyl-phosphine oxide and its combination with epoxy resins, as in WO-A
- the tetrakis-hydroxyalkyl phosphonium salts are particularly preferred.
- the bis-di-ortho-xylylester are particularly preferred with piperazine as a bridge member.
- phosphinate esters such as
- Benzene monophenyl ester derivatives or phosphaphenanthrene derivatives for example, 9,10-dihydro-9-0xa-10-phosphaphenanthrene-10-oxide or 6H-dibenzo (c, e) (1,2) -oxa-hosphorin-6-one) derivatives, such as shown in the following formulas.
- dihydro-oxa-phospha-anthracene can also be used oxide (on) can be used. An overview of this can be found in WO-A 2008/1 19693.
- R ' CH 3 , nC 4 H 9 , or cC 6 Hn
- polyols polyols, aminouracils, POSS compounds, trishydroxyethyl isocyanurate, melamine cyanurate, expandable graphite or mixtures thereof.
- POSS compounds polyhedral oligomeric silsesquioxanes
- POSS derivatives based on methylsiloxane.
- Triazine polymers having piperazine-1,4-diyl bridge members and morpholine-1-yl end groups may be included in the flame retardants of the present invention.
- the following additives may be present in the flame retardants of the present invention: bis-azine pentaerythritol diphosphate salts, hexa-aryloxy triphosphazenes, polyaryloxy phosphazenes and siloxanes, for example of the general formula (R 2 SiO) r or (RSiO-i, 5 ) r.
- mixtures of two or more of the compounds described above may also be present in the compositions of the present invention.
- Particularly preferred are the following combinations.
- MZP or MAP 2 (melamine zinc phosphate / melamine aluminum diphosphate)
- M 2 ZP 2 or M 2 AP 3 (Dimelamin-zinc diphosphate / Dimelamin-aluminum triphosphate) and Mg (2 '-hydroxy [1, 1' -biphenyl-2-yl-2-phosphinate) 2, Zn (2 '-hydroxy [1, 1' -biphenyl-2-yl-2-phosphinate) 2,
- MZP or MAP 2 (melamine zinc phosphate / melamine aluminum diphosphate)
- M 2 ZP 2 or M 2 AP 3 (dimelamine zinc diphosphate / dimelamine aluminum triphosphate)
- MZP or MAP 2 melamine-zinc phosphate / melamine Aluminiumdiphosphat
- Mg 2 '-hydroxy [, 1' -biphenyl-2-yl-2-phosphinate
- M 2 ZP 2 or M 2 AP 3 (Dimelamin-zinc diphosphate / Dimelamin-aluminum triphosphate) and Mg (2 '-hydroxy [1, 1' -biphenyl-2-yl-2-phosphinate) 2,
- MZP or MAP 2 (melamine zinc phosphate / melamine aluminum diphosphate) and Mg (2 '-hydroxy [1, 1' -biphenyl-2-yl-2-phosphinate) 2
- M 2 ZP 2 or M 2 AP 3 (Dimelamin-zinc diphosphate / Dimelamin-Aluminiumtripho ⁇ and Mg (2 '-hydroxy [, 1' -biphenyl-2-yl-2-phosphinate) 2,
- a particular embodiment of the invention relates to the use of the compositions described above, which -phosphinates inventive metal-2-hydroxydiphenyl-2, 'and the metal phosphonates prepared therefrom by cyclization contained in a polymer as a flame retardant.
- the present invention thus further relates to compositions, as described above, which additionally contain a polymer or a polymer mixture.
- the composition described above comprising component (i), (ii-a) and / or (ii-b) is first prepared and this composition incorporated into the polymer or the polymer mixture.
- the invention also relates to a process for the preparation of flame-retardant polymer molding compositions, characterized in that the stabilized flame retardants according to the invention are homogenized with the polymer granules and any additives in a compounding unit at higher temperatures in the polymer melt and then the homogenized polymer strand is withdrawn, cooled and portioned.
- the resulting granules are e.g. dried at 90 ° C in a convection oven.
- the compounding unit preferably comes from the group of single-screw extruders, multizone screws or twin-screw extruders.
- Compounding units are single-screw extruders or single-screw extruders, e.g. the company Berstorff GmbH, Hannover and or the company Leistritz, Nuremberg,
- Short-Compression Screws Ko-Kneader eg Fa.
- Planetary roller extruder e.g. Entex, Bochum and / or degassing extruders and / or cascade extruders and / or Maillefer screws; Compounder with counter-rotating twin screw e.g. Complex 37- or -70-types of the company Krauss-Maffei Berstorff.
- the polymer is typically a thermoplastic, which is preferably selected from the group consisting of polyamide, polycarbonate, polyolefin, polystyrene, polyester, polyvinyl chloride, polyvinyl alcohol, ABS and polyurethane, or a
- Duroplast is, which is preferably selected from the group consisting of epoxy resin (with hardener), phenolic resin and melamine resin.
- thermosets and / or thermosets, in which the azine-metal phosphate according to the invention is used as flame retardant.
- Polymers of mono- and diolefins e.g. Polypropylene, polyisobutylene, polybutene-1, poly-4-methylpentene-1, polyvinylcyclohexane, polyisoprene or
- Polybutadiene and polymers of cycloolefins e.g. of cyclopentene or norbornene and polyethylene (also cross-linked), e.g. High Density Polyethylene (HDPE) or High Molecular Weight (HDPE-HMW), High Density Polyethylene with Ultra-High Molecular Weight (HDPE-UHMW), Medium Density Polyethylene (MDPE), Low Density Polyethylene (LDPE) and Linear Low Density Polyethylene ( LLDPE), (VLDPE) and (ULDPE) as well as copolymers of ethylene and vinyl acetate (EVA);
- HDPE High Density Polyethylene
- HDPE-HMW High Molecular Weight
- HDPE-UHMW High Density Polyethylene with Ultra-High Molecular Weight
- MDPE Medium Density Polyethylene
- LDPE Low Density Polyethylene
- LLDPE Linear Low Density Polyethylene
- VLDPE Linear Low Density Polyethylene
- ULDPE Linear Low Density
- Polystyrenes poly (p-methylstyrene), poly ( ⁇ -methylstyrene);
- Polybutadiene and (meth) acrylonitrile such as ABS and MBS
- Halogen-containing polymers for example polychloroprene, polyvinyl chloride (PVC);
- PVDC Polyvinylidene chloride
- Vinyl chloride / vinyl acetate or vinyl chloride / vinyl acetate Vinyl chloride / vinyl acetate.
- PMMA polymethyl methacrylates
- PAN polyacrylonitrile
- Polymers of unsaturated alcohols and amines or their Azylderivaten or acetals such.
- Polyvinyl alcohol (PVA) polyvinyl acetates, stearates, benzoates or maleates, polyvinyl butyral, polyallyl phthalates and polyallyl melamines;
- cyclic ethers such as polyalkylene glycols, polyethylene oxides, polypropylene oxides and their copolymers with bisglycidyl ethers;
- Polyacetals such as polyoxymethylene (POM) and polyurethane and acrylate modified polyacetals;
- Polyamides and copolyamides derived from diamines and dicarboxylic acids and / or from aminocarboxylic acids or the corresponding lactams e.g. Polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 12/12, polyamide 11, polyamide 12, aromatic polyamides derived from m-xylylenediamine and adipic acid and copolyamides modified with EPDM or ABS.
- Copolyamides are derived from ⁇ -caprolactam, adipic acid, sebacic acid, dodecanoic acid, isophthalic acid, terephthalic acid, hexamethylenediamine,
- Tetramethylenediamine 2-methyl-pentamethylenediamine, 2,2,4-trimethyl-hexamethylenediamine, 2,4,4-trimethylhexamethylenediamine, m-xylylenediamine or bis (3-methyl-4-aminocyclohexyl) methane;
- Polyureas polyimides, polyamideimides, polyetherimides, polyesterimides, polyhydantoins and polybenzimidazoles.
- Hydroxycarboxylic acids or the corresponding lactones e.g.
- Polyhydroxybenzoates polylactic acid esters and polyglycolic acid esters
- polyketones Mixtures or alloys of above-mentioned polymers, eg PP / EPDM, PA / EPDM or ABS, PVC / EVA, PVC / ABS, PBC / MBS, PC / ABS, PBTP / ABS, PC / AS, PC / PBT, PVC / CPE, PVC / Acrylate, POM / Thermoplastic PUR, PC / Thermoplastic PUR, POM / Acrylate, POM / MBS, PPO / HIPS, PPO / PA6.6 and Copolymers, PA / HDPE, PA / PP, PA / PPO, PBT / PC / ABS or PBT / PET / PC, as well as TPE-O, TPE-S and TPE-E;
- Thermosets such as PF, MF or UF or mixtures thereof;
- Wood-plastic composites as well as polymers based on PLA, PHB and starch.
- PA Preference is given to PA, PET, PBT, PUR, PC and epoxy resins. Particularly preferred are glass fiber reinforced PA and PBT.
- the concentration of the flame retardant preparations according to the invention consisting of metal (thio) phosphinate or metal (thio) phosphonate (i) and the additional metal-containing component (ii-a) and / or the metal-free component (ii-b) is preferably in a polymer or a polymer mixture 0.1 to 60 wt .-%, based on the polymer or the polymer mixture.
- Component ratio in the composition consisting of component (i) to the co-components (ii-a) and / or (ii-b) is preferably in the range of 1: 1 to 1: 4.
- Polymer material according to the invention further contain fillers, which are preferably selected from the group consisting of metal hydroxides and / or
- Metal oxides preferably alkaline earth metal hydroxides, for example
- Minerals such as wollastonite, silica such as quartz, mica, feldspar and titanium dioxide, alkaline earth metal silicates and alkali metal silicates, carbonates,
- fillers can impart further desired properties to the polymer material of the invention.
- a filler preferably calcium carbonate and talc, clay, mica, silica, calcium sulfate, barium sulfate, pyrite, glass fiber, glass beads, glass particles and glass beads, wood flour, cellulose powder, carbon black, graphite, chalk and pigments.
- the mechanical stability can be increased or dyed by adding dyes to the plastic.
- the polymer materials may contain further additives, such as antioxidants, light stabilizers, process auxiliaries,
- Viscosity improvers impact modifiers and in particular compatibilizers and dispersants.
- foaming agents can be added to the polymer in addition to the azine metal phosphate of the present invention.
- Foaming agents are preferably melamine, melamine-formaldehyde resins, urea derivatives such as urea, thiourea, guanamine, benzoguanamine, acetoguanamine and succinylguanamine, dicyandiamide, guanidine and guanidine sulfamate and also other guanidine salts or allantoins and glycolurils.
- a polymer containing the azine metal phosphate according to the invention may also comprise antidripping agents, in particular
- Polytetrafluoroethylene base included.
- concentration of such anti-dripping agents is preferably 0.01 to 15 wt .-%, based on the processed
- Example 1 shows that the conductivity of the product according to the invention is lower by a factor of 4.7 and is therefore more suitable in electronic applications.
- Example 3B Spray Method
- the drying can be carried out by spraying.
- the nutschfeuchte filter cake is suspended in water and the resulting slurry dried by spray granulation at 70-80 ° C.
- Magnesium and calcium salts of 10-hydroxy-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide were prepared similarly as in Example 7, but starting from magnesium hydroxide or calcium hydroxide (mp> 300 ° C ).
- Example 13 (Use as flame retardant in PA)
- PA 6.6 (Durethan A30S, LANXESS); Glass fiber (Thermo Flow ® 671; 10 mx4mm; Fa John Manville.); MPP melamine polyphosphate (Melapur 200; BASF.), (2 '-hydroxy [1, 1' -biphenyl-2-yl-2-phosphinate) 2 Zn (Example 3), Dimelamin- zinc diphosphate (own product).
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Abstract
L'invention concerne un procédé de production de métal-2-Hydroxydiphényl-2'-(Thio)phosphinates de formule (I), à partir de (6H)-Dibenz(c,e)(1,2)-oxaphosphorin-6-on(thion) (II) et de métal(hydr)oxydes ou de carbonates métalliques (basiques), et de métal(Thio)phosphonats (III) obtenus par cyclisation à partir des précédents, Mt = Cu, Ca, Mg, Zn, Mn, Fe, AI, Co, Ni, Sn, Zr, TiO, ZrO, Ce, MoO, W02, VO, B, Si, La, Ti, Bi oder Sb X = H ou OH, Y = O ou S et n = 2 ou 3, ainsi que leurs compositions et l'utilisation desdites compositions comme agents ignifuges pour des polymères, du papier, des textiles ou des composites bois-plastique (CPC).
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PCT/EP2012/004330 WO2014060004A1 (fr) | 2012-10-16 | 2012-10-16 | Procédé de production de métal-hydroxydiphényl-2' -(thio)phosphinates et de métal-diphénylène-(thio)phosphonates, compositions les contenant et leur utilisation comme agents ignifuges |
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WO2021048155A1 (fr) * | 2019-09-11 | 2021-03-18 | Clariant International Ltd | Composition ignifuge, composition de moulage polymère la comprenant et son utilisation |
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CN112409693B (zh) * | 2020-11-26 | 2023-05-09 | 浙江旭森阻燃剂股份有限公司 | 具有良好阻燃和加工性能的无卤阻燃剂及阻燃树脂组合物 |
CN112409693A (zh) * | 2020-11-26 | 2021-02-26 | 浙江旭森非卤消烟阻燃剂有限公司 | 具有良好阻燃和加工性能的无卤阻燃剂及阻燃树脂组合物 |
CN112625340A (zh) * | 2020-12-01 | 2021-04-09 | 张家港优全汽配有限公司 | 一种纤维增强聚丙烯复合材料、制备方法及其应用 |
CN115322439A (zh) * | 2022-05-18 | 2022-11-11 | 沈阳工业大学 | 利用水镁石制备的用于环氧树脂的复配阻燃剂的制备方法 |
CN115322439B (zh) * | 2022-05-18 | 2023-06-16 | 沈阳工业大学 | 利用水镁石制备的用于环氧树脂的复配阻燃剂的制备方法 |
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