US20030040643A1 - Process for producing phenoxyphosphazene compound, flame- retardant resin composition, and flame-retardant resin molding - Google Patents
Process for producing phenoxyphosphazene compound, flame- retardant resin composition, and flame-retardant resin molding Download PDFInfo
- Publication number
- US20030040643A1 US20030040643A1 US10/030,439 US3043902A US2003040643A1 US 20030040643 A1 US20030040643 A1 US 20030040643A1 US 3043902 A US3043902 A US 3043902A US 2003040643 A1 US2003040643 A1 US 2003040643A1
- Authority
- US
- United States
- Prior art keywords
- phenoxyphosphazene compound
- resin
- compound
- phenoxyphosphazene
- parts
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 246
- 238000000034 method Methods 0.000 title claims abstract description 42
- 239000011342 resin composition Substances 0.000 title claims abstract description 40
- 229920005989 resin Polymers 0.000 title claims description 98
- 239000011347 resin Substances 0.000 title claims description 98
- 239000003063 flame retardant Substances 0.000 title claims description 25
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims description 23
- 238000000465 moulding Methods 0.000 title claims description 17
- -1 diazoalkanes Chemical class 0.000 claims abstract description 68
- 229920003002 synthetic resin Polymers 0.000 claims abstract description 40
- 239000000057 synthetic resin Substances 0.000 claims abstract description 40
- 239000003463 adsorbent Substances 0.000 claims abstract description 38
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 14
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000004927 clay Substances 0.000 claims abstract description 11
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims abstract description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000000741 silica gel Substances 0.000 claims abstract description 10
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 10
- 229910052987 metal hydride Inorganic materials 0.000 claims abstract description 9
- 150000004681 metal hydrides Chemical class 0.000 claims abstract description 9
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 8
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000010457 zeolite Substances 0.000 claims abstract description 8
- 150000002905 orthoesters Chemical class 0.000 claims abstract description 7
- 150000004764 thiosulfuric acid derivatives Chemical class 0.000 claims abstract description 7
- 239000004593 Epoxy Substances 0.000 claims abstract description 6
- 150000002596 lactones Chemical class 0.000 claims abstract description 6
- 229920005668 polycarbonate resin Polymers 0.000 claims description 22
- 239000004431 polycarbonate resin Substances 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 20
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- 125000004122 cyclic group Chemical group 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000004132 cross linking Methods 0.000 claims description 6
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 4
- 235000019345 sodium thiosulphate Nutrition 0.000 claims description 4
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 4
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 claims description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 12
- 238000002845 discoloration Methods 0.000 abstract description 8
- 238000010348 incorporation Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 66
- 239000004417 polycarbonate Substances 0.000 description 58
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 229910052783 alkali metal Inorganic materials 0.000 description 47
- 239000008188 pellet Substances 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 45
- 239000004810 polytetrafluoroethylene Substances 0.000 description 41
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 40
- 239000000203 mixture Substances 0.000 description 35
- 239000004793 Polystyrene Substances 0.000 description 32
- 229920002223 polystyrene Polymers 0.000 description 32
- 238000004458 analytical method Methods 0.000 description 29
- 238000000354 decomposition reaction Methods 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 150000001340 alkali metals Chemical class 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000000835 fiber Substances 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 239000007864 aqueous solution Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 229940031826 phenolate Drugs 0.000 description 17
- 239000000460 chlorine Substances 0.000 description 16
- 229910052801 chlorine Inorganic materials 0.000 description 14
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- 230000021736 acetylation Effects 0.000 description 13
- 238000006640 acetylation reaction Methods 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 230000004580 weight loss Effects 0.000 description 12
- 238000001514 detection method Methods 0.000 description 11
- 238000002347 injection Methods 0.000 description 11
- 239000007924 injection Substances 0.000 description 11
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000654 additive Substances 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 229910052698 phosphorus Inorganic materials 0.000 description 9
- 239000011574 phosphorus Substances 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 7
- 239000011256 inorganic filler Substances 0.000 description 7
- 229910003475 inorganic filler Inorganic materials 0.000 description 7
- 229920000647 polyepoxide Polymers 0.000 description 7
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229920001955 polyphenylene ether Polymers 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000002411 adverse Effects 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 239000011259 mixed solution Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 229920001187 thermosetting polymer Polymers 0.000 description 5
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VOQCNVFFBTVKCW-UHFFFAOYSA-N CN=P(C)(C)C Chemical compound CN=P(C)(C)C VOQCNVFFBTVKCW-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000007774 longterm Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229920005992 thermoplastic resin Polymers 0.000 description 4
- 239000013638 trimer Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000000378 calcium silicate Substances 0.000 description 3
- 229910052918 calcium silicate Inorganic materials 0.000 description 3
- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 229910003002 lithium salt Inorganic materials 0.000 description 3
- 159000000002 lithium salts Chemical class 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- PEJQKHLWXHKKGS-UHFFFAOYSA-N 2,2,4,4,6,6,8,8-octachloro-1,3,5,7-tetraza-2$l^{5},4$l^{5},6$l^{5},8$l^{5}-tetraphosphacycloocta-1,3,5,7-tetraene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 PEJQKHLWXHKKGS-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- HZAWPPRBCALFRN-UHFFFAOYSA-N CC1=CC=C(CC2=CC=C(C)C=C2)C=C1 Chemical compound CC1=CC=C(CC2=CC=C(C)C=C2)C=C1 HZAWPPRBCALFRN-UHFFFAOYSA-N 0.000 description 2
- PYEWTKHPXOSFPI-UHFFFAOYSA-N CN=P(C)(Cl)Cl Chemical compound CN=P(C)(Cl)Cl PYEWTKHPXOSFPI-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000004640 Melamine resin Substances 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000011805 ball Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001642 boronic acid derivatives Chemical class 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 230000002542 deteriorative effect Effects 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 229920012128 methyl methacrylate acrylonitrile butadiene styrene Polymers 0.000 description 2
- 239000010445 mica Substances 0.000 description 2
- 229910052618 mica group Inorganic materials 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical class CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 description 2
- 239000004843 novolac epoxy resin Substances 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000005011 phenolic resin Substances 0.000 description 2
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- XAVQZBGEXVFCJI-UHFFFAOYSA-M lithium;phenoxide Chemical compound [Li+].[O-]C1=CC=CC=C1 XAVQZBGEXVFCJI-UHFFFAOYSA-M 0.000 description 1
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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
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- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
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- 239000005020 polyethylene terephthalate Substances 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- SATVIFGJTRRDQU-UHFFFAOYSA-N potassium hypochlorite Chemical compound [K+].Cl[O-] SATVIFGJTRRDQU-UHFFFAOYSA-N 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 230000002265 prevention Effects 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
- 229960000380 propiolactone Drugs 0.000 description 1
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- 238000006462 rearrangement reaction Methods 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
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- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- GROMGGTZECPEKN-UHFFFAOYSA-N sodium metatitanate Chemical compound [Na+].[Na+].[O-][Ti](=O)O[Ti](=O)O[Ti]([O-])=O GROMGGTZECPEKN-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
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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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
-
- 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
- C08K5/5399—Phosphorus bound to nitrogen
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- 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
- C07F9/6581—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 nitrogen atoms with or without oxygen or sulfur atoms, as ring hetero atoms
- C07F9/65812—Cyclic phosphazenes [P=N-]n, n>=3
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- 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 present invention relates to a process for the preparation of phenoxyphosphazene compounds, flame-retardant resin compositions and flame-retardant resin molded articles.
- Phenoxyphosphazene compounds are the oligomers or polymers which are prepared by reacting a dichlorophosphazene compound with an alkali metal salt of a phenol compound.
- the use of these compounds as additives, modifiers, etc., for synthetic resins has been heretofore studied.
- Phenoxyphosphazene compounds can impart high flame retardancy, thermal stability, molding processability and other properties to synthetic resins.
- phenoxyphosphazene compounds have a serious drawback: they discolor synthetic resins when added thereto.
- a phenoxyphosphazene compound may deteriorate the heat resistance, weathering resistance, discoloration resistance, chemical resistance and other properties of the synthetic resin in long-term storage, although such deterioration may not be evident shortly after the addition.
- resin compositions prepared by adding a phenoxyphosphazene compound to a polycarbonate resin or a mixed resin of a polycarbonate resin and another resin undergo a decrease in molecular weight of the polycarbonate resins during long-term storage. Inevitably, this results in greatly lowered transparency, change in hue such as whiteness, etc., of the polycarbonate resins.
- Phenoxyphosphazene compounds are usually washed with an aqueous solution containing an acid such as hydrochloric acid, sulfuric acid or the like, an aqueous solution containing an alkali such as sodium hydroxide, sodium carbonate or the like or water.
- an aqueous solution containing an acid such as hydrochloric acid, sulfuric acid or the like
- an aqueous solution containing an alkali such as sodium hydroxide, sodium carbonate or the like or water.
- An object of the present invention is to provide a phenoxyphosphazene compound which prevents discoloration of a synthetic resin when added thereto.
- Another object of the present invention is to provide a phenoxyphosphazene compound which can be added to a synthetic resin without deteriorating the properties of the synthetic resin such as heat resistance, weathering resistance, discoloration resistance, chemical resistance and the like even when stored for a long time.
- Another object of the present invention is to provide a phenoxyphosphazene compound which can be added to a polycarbonate resin or a mixture of a polycarbonate resin and another resin without substantially reducing the molecular weight, the transparency, hue such as whiteness, etc. of the polycarbonate resin.
- Another object of the present invention is to provide a phenoxyphosphazene compound which does not corrode a molding device when it is added to a synthetic resin and the resulting resin composition is molded.
- Another object of the present invention is to provide a phenoxyphosphazene compound which can impart to a molded article of a resin composition containing a synthetic resin, when added thereto, excellent flame retardancy, thermal stability, molding processability and like desired properties.
- Another object of the present invention is to provide a process for preparation of such a phenoxyphosphazene compound.
- the present invention was accomplished based on these findings.
- the present invention provides a process for preparation of an improved phenoxyphosphazene compound by treating a phenoxyphosphazene compound with (a) at least one adsorbent selected from activated carbon, silica gel, activated alumina, activated clay, synthetic zeolite and macromolecular adsorbents, or (b) at least one reagent or reactant selected from metal hydrides, hydrazine, hypochlorites, thiosulfates, dialkyl sulfuric acids, ortho esters, diazoalkanes, lactones, alkanesultones, epoxy compounds and hydrogen peroxide or (c) both the adsorbent and reagent.
- adsorbent selected from activated carbon, silica gel, activated alumina, activated clay, synthetic zeolite and macromolecular adsorbents
- reagent or reactant selected from metal hydrides, hydrazine, hypochlorites, thiosulfates,
- the present invention provides a process for preparation of an improved phenoxyphosphazene compound by treating a phenoxyphosphazene compound with at least one absorbent selected from activated carbon, silica gel, activated alumina, activated clay, synthetic zeolite and macromolecular adsorbents.
- the present invention provides a process for preparation of an improved phenoxyphosphazene compound by treating a phenoxyphosphazene compound with at least one reagent selected from metal hydrides, hydrazine, hypochlorites, thiosulfates, dialkyl sulfuric acids, ortho esters, diazoalkanes, lactones, alkanesultones, epoxy compounds and hydrogen peroxide.
- at least one reagent selected from metal hydrides, hydrazine, hypochlorites, thiosulfates, dialkyl sulfuric acids, ortho esters, diazoalkanes, lactones, alkanesultones, epoxy compounds and hydrogen peroxide.
- the present invention provides a phenoxyphosphazene which can inhibit the discoloration of a synthetic resin when added thereto.
- the present invention provides a phenoxyphosphazene compound which can impart highly improved flame retardancy, thermal stability, molding processability and other properties to a molded article of a resin composition containing the phenoxyphosphazene compound and a synthetic resin.
- the present invention provides a phenoxyphosphazene compound which can be added to a synthetic resin without deteriorating the properties of the synthetic resin such as heat resistance, weathering resistance, discoloration resistance, chemical resistance and the like even when the resulting resin composition is stored for a long time.
- the present invention provides a phenoxyphosphazene compound which can be added to a polycarbonate resin or a mixture of a polycarbonate resin and another resin without substantially reducing the molecular weight of the polycarbonate resin and changing transparency and the hue such as whiteness of the polycarbonate resin.
- the present invention provides a phenoxyphosphazene compound which does not corrode a molding device when a resin composition containing synthetic resin and the phenoxy phosphazene compound is molded.
- the present invention provides a flame retardant which contains the above phenoxyphosphazene compound.
- the present invention provides a flame-retardant resin composition prepared by adding the above phenoxyphosphazene compound to a synthetic resin.
- the present invention provides a flame-retardant resin molded article prepared by molding the above flame-retardant resin composition.
- the term “improved” means modifying the properties of a phenoxyphosphazene compound so that the phenoxyphosphazene compound does not deteriorate the properties of a synthetic resin contained in a resin composition when used for the resin composition which is stored for a long time. More specifically, the term “improved” means, for example, lowering the acid value of a phenoxyphosphazene compound to a level less than 0.025.
- Phenoxyphosphazene compounds which are treated according to the present invention are not limited insofar as they are obtained by the reaction between a dichlorophosphazene compound and a phenol compound or its alkali metal salt, and include a wide variety of known compounds.
- Such phenoxyphosphazene compounds include the following:
- Cyclic phenoxyphosphazene compounds (hereinafter referred to as “cyclic phenoxyphosphazene compound (1)”) represented by formula (1)
- m is an integer from 3 to 25; and Ph represents a phenyl group.
- Chain-like phenoxyphosphazene compounds (hereinafter referred to as “chain-like phenoxyphosphazene compound (2)”) represented by formula (2)
- X 1 represents a group —N ⁇ P(OPh) 3 or a group —N ⁇ P(O)OPh
- Y 1 represents a group —P(OPh) 4 or a group —P(O)(OPh) 2
- n is an integer from 3 to 10000
- Ph is as defined above.
- crosslinked phenoxyphosphazene compound (3) Crosslinked phenoxyphosphazene compounds obtained by crosslinking at least one phosphazene compound selected from the cyclic phenoxyphosphazene compounds (1) and the chain-like phenoxyphosphazene compounds (2) with at least one crosslinking group selected from o-phenylene group, m-phenylene group, p-phenylene group and a bisphenylene group which is represented by formula (3)
- A represents —C(CH 3 ) 2 —, —SO 2 —, —S— or —O—; and a is 0 or 1, the compound (3) having the following characteristics:
- each of the crosslinking groups is interposed between two oxygen atoms left after the elimination of phenyl groups of the phosphazene compound;
- the amount of the phenyl groups in the crosslinked compound is 50 to 99.9% based on the total amount of the phenyl groups in the phosphazene compound (1) and/or (2);
- the terminal groups X 1 and Y 1 in formula (2) may vary in accordance with the reaction conditions and other factors.
- the reaction is carried out under ordinary conditions, e.g., under mild conditions in a non-aqueous system, the resulting product will have a structure wherein X 1 is —N ⁇ P(OPh) 3 and Y 1 is —P(OPh) 4 .
- the resulting product will be a mixture of compounds, some having a structure wherein X 1 is —N ⁇ P(OPh) 3 and Y 1 is —P(OPh) 4 and others having a structure wherein X 1 is —N ⁇ P(O)OPh and Y 1 is —P(O)(OPh) 2 .
- the phrase “to have no free hydroxyl groups in the molecule” means that the amount of free hydroxyl groups is less than the detectable limit, when measured according to the acetylation process using acetic anhydride and pyridine as described on page 353 of “Analytical Chemistry Handbook”, revised 3rd edition, Japan Analytical Chemistry Academy, Maruzen Co., (1981).
- the term “detectable limit” herein means the minimum amount detectable as hydroxyl equivalents per gram of a test sample (crosslinked phenoxyphosphazene compound (3)), more specifically 1 ⁇ 10 ⁇ 6 hydroxyl equivalents/gram.
- the resulting amount includes the amount of hydroxyl groups in the residual phenol used as a starting material. Since the quantity of the residual phenol can be determined by high performance liquid chromatography, the amount of only free hydroxyl groups in the crosslinked phenoxyphosphazene compound (3) can be precisely determined.
- the cyclic phenoxyphosphazene compound (1) and chain-like phenoxyphosphazene compound (2) are prepared by reacting a dichlorophosphazene compound with an alkali metal phenolate.
- cyclic dichlorophosphazene compound (4) cyclic dichlorophosphazene compound (4)
- chain-like dichlorophosphazene compound (5) represented by formula (5)
- X 2 represents a group —N ⁇ PCl 3 or group —N ⁇ P(O)Cl
- Y 2 represents a group —P(Cl) 4 or group —P(O)Cl 2
- n is as defined above, and the like.
- the dichlorophosphazene compounds may be used singly or in combinations of two or more species. At least one of cyclic dichlorophosphazene compounds and at least one of chain-like dichlorophosphazene compounds may be used in combination.
- Dichlorophosphazene compounds can be prepared, for example, by the processes described in H. R. Allcock, “Phosphorus-Nitrogen Compounds”, Academic Press, (1972); J. E. Mark, H. R. Allcock, R. West, “Inorganic Polymers”, Prentice-Hall International Inc., (1992), etc. For instance, ammonium chloride and phosphorus pentachloride (or ammonium chloride, phosphorus trichloride and chlorine) are reacted in chlorobenzene or tetrachloroethane at about 120 to about 130° C.
- dichlorophosphazene compounds (4) in which m is 3 to 25 and chain-like dichlorophosphazene compounds (5) in which n is 3 to 25 can be prepared.
- dichiorophosphazene compounds (dichlorophosphazene oligomer) are usually obtained as mixtures.
- alkali metal phenolates are useful. Examples are alkali metal phenolates (hereinafter referred to as “alkali metal phenolate (6)”) represented by formula (6).
- M represents an alkali metal
- alkali metals represented by M are sodium, potassium, lithium and the like.
- alkali metal phenolate (6) are sodium phenolate, potassium phenolate, lithium phenolate and the like.
- Alkali metal phenolates may be used singly or in combinations of two or more species.
- the crosslinked phenoxyphosphazene compound (3) can be prepared, for example, by mixing a dichlorophosphazene compound with an alkali metal phenolate and diphenolate to cause a reaction (first step) and further reacting the resulting compound with an alkali metal phenolate (second step).
- Useful dichlorophosphazene compounds include those mentioned above. They may be used in combinations of two or more species, and cyclic and chain-like dichlorophosphazene compounds may be used in combination.
- Useful alkali metal phenolates include those mentioned above, which may be used in combinations of two or more species.
- alkali metal diphenolate (7) o-, m- and p-substituted alkali metal diphenolates (hereinafter referred to as “alkali metal diphenolate (7)”) represented by formula (7),
- alkali metal diphenolates (hereinafter referred to as “alkali metal diphenolate (8)”) represented by formula (8),
- alkali metal diphenolate (7) two groups —O—M (wherein M is as defined above) may positionally in ortho, meta or para relation.
- alkali metal diphenolate (7) examples include resorcinol, hydroquinone, catechol and like alkali metal salts. Among these, sodium salts and lithium salts are preferable.
- the alkali metal diphenolate (7) may be used singly or in combinations of two or more species.
- alkali metal diphenolate (8) examples include 4,4′-isopropylidenediphenol (bisphenol-A), 4,4′-sulfonyldiphenol (bisphenol-S), 4,4′-thiodiphenol, 4,4′-oxydiphenol, 4,4′-diphenol and like alkali metal salts. Among these, sodium salts and lithium salts are preferable.
- the alkali metal diphenolate (8) may be used singly or in combinations of two or more species. At least one of the alkali metal diphenolate (7) and at least one of the alkali metal diphenolate (8) may be used in combination.
- alkali metal phenolate and alkali metal diphenolate in such amounts that not all chlorine atoms in the dichlorophosphazene compound are consumed by the reaction with alkali metal phenolate and alkali metal diphenolate, namely, some chlorine atoms in the dichlorophosphazene compound remain as they are after the reaction with alkali metal phenolate and alkali metal diphenolate. Consequently, —O—M groups (wherein M is as defined above) at both sides in alkali metal diphenolate combine with phosphorus atoms in the dichlorophosphazene compound.
- the total amount of alkali metal phenolate and alkali metal diphenolate used is usually about 0.05 to about 0.9 equivalents, preferably about 0.1 to about 0.8 equivalents, relative to the chlorine content of the dichlorophosphazene compound.
- alkali metal phenolate in an amount such that all the chlorine atoms in the compound obtained by the first step can be consumed by the reaction with alkali metal phenolate.
- the alkali metal phenolate is used usually in an amount of about 1 to about 1.5 equivalents, preferably about 1 to about 1.2 equivalents, relative to the chlorine content of the dichlorophosphazene compound.
- the ratio of alkali metal diphenolate (the total amount thereof used in the first and second steps) to alkali metal phenolate (alkali metal diphenolate alkali metal phenolate, in molar ratio) is usually about 1/2000 to about 1/4, preferably 1/20 to 1/6.
- the reactions in the first step and the second step are usually carried out at a temperature ranging from room temperature to about 150° C., preferably about 80 to about 140° C.
- the reactions are completed usually in about 1 to about 12 hours, preferably about 3 to about 7 hours.
- organic solvent examples include aromatic hydrocarbons such as benzene, toluene, xylene, etc.; halogenated aromatic hydrocarbons such as monochlorobenzene, dichlorobenzene, etc.
- the decomposition temperature of the crosslinked phenoxyphosphazene compound (3) obtained by the above reactions is usually in the range of 250 to 350° C.
- the proportion of the phenyl groups in the crosslinked phenoxyphosphazene compound (3) is 50 to 99.9%, preferably 70 to 90%, based on the total amount of the phenyl groups in the cyclic phenoxyphosphazene compound (1) and/or chain-like phenoxyphosphazene compound (2).
- the treatment of a phenoxyphosphazene compound using an adsorbent may be conducted in any known manner which can bring the adsorbent and phenoxyphosphazene compound into contact.
- an adsorbent and a phenoxyphosphazene compound are mixed in a vessel (batch process), or a phenoxyphosphazene compound is passed through an adsorbent filled in a column or a like container.
- An adsorbent useful in the present invention is at least one member selected from activated carbon, silica gel, activated alumina, activated clay, synthetic zeolite and macromolecular adsorbents.
- Activated carbon, silica gel, activated alumina, activated clay, synthetic zeolite and macromolecular adsorbents can be selected from a wide variety of known products.
- Preferable activated carbons are those activated with chemicals and those activated with steam.
- Activated carbons may be in the shape of cylinders, crushed particles, granules, balls or powder.
- Silica gel may be in any shape of minute particles, small particles, medium particles and large granules.
- Activated alumina may be acidic, basic or neutral.
- Activated clay may be powdery or granular.
- Useful synthetic zeolite can be selected from a wide range of commercial products, and may have a pore diameter ranging from about 3 ⁇ to about 10 ⁇ .
- the pore diameter thereof can be about 3 ⁇ , about 4 ⁇ , about 5 ⁇ and about 10 ⁇ .
- Synthetic zeolite may be in any form of pellets, beads and a powder.
- Useful macromolecular adsorbents include a wide range of known synthetic resins which have an adsorbing ability. Examples include crosslinked polymers which comprise styrene and divinylbenzene, crosslinked polymers which comprises methacrylate ester and ethylene glycol dimethacrylate and the like. Examples of commercially available macromolecular adsorbents include AMBERLITE XAD (trade name, manufactured by ROHM AND HAAS COMPANY), DIAION HP (trade name, manufactured by MITSUBISHI CHEMICAL CORPORATION), etc.
- the amount of an adsorbent used is not limited and may be suitably selected from a wide range depending on the type and amount of the phenoxyphosphazene compound, the type of the adsorbent and other conditions.
- the amount is usually 1 to 50 parts by weight, preferably 2 to 25 parts by weight, based on 100 parts by weight of the phenoxyphosphazene compound.
- the amount of adsorbent added is lower than 1 part by weight, the effect achieved by the adsorbent is likely to be unsatisfactory.
- the amount is much higher than 50 parts by weight, the adsorbent adsorbs not only impurities but also phenoxyphosphazene compounds. This may result in a lowered yield.
- the amount of adsorbent used is not restricted.
- the adsorbent is placed in a column in an amount suitable for continuous stable column operation, and the adsorbent may be replaced or reactivated when the adsorbing ability of the adsorbent is reduced.
- a phenoxyphosphazene compound and an adsorbent are brought into contact in a state that the phenoxyphosphazene compound is melt, or in a state that the phenoxyphosphazene compound is dissolved in a solvent.
- the solvent may be selected from known solvents which can dissolve the phenoxyphosphazene compound and do not adversely affect the function of the adsorbent.
- reaction solvents for the dichlorophosphazene compound and the alkali metal phenolate include aromatic hydrocarbons such as benzene, toluene, xylene, etc., halogenated aromatic hydrocarbons such as monochlorobenzene, dichlorobenzene, etc.
- aromatic hydrocarbons such as benzene, toluene, xylene, etc.
- halogenated aromatic hydrocarbons such as monochlorobenzene, dichlorobenzene, etc.
- the same solvent same as the above may be used.
- solvents to be used include, in addition to the solvents mentioned above, halogenated hydrocarbons such as chloroform, carbon tetrachloride, chloroethane and the like; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and the like; alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, tert-butanol and the like; esters such as methyl formate, ethyl formate, propyl formate, butyl formate, methyl acetate, ethyl acetate, propyl acetate, butyl acetate and the like; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, dioxane, trioxane and
- solvents may be used singly or in combinations of two or more species.
- chloroform, acetone and tetrahydrofuran are preferable.
- the concentration of the phenoxyphosphazene compound is not restricted. However, considering the ease of operation, the concentration is preferably 1 to 90% by weight, more preferably 5 to 80% by weight.
- the temperature preferably ranges from the melting point of the phenoxyphosphazene compound to about 200° C.
- the treatment may be carried out at any temperature at which the solvent can dissolve the phenoxyphosphazene compound.
- the temperature usually ranges from 0° C. to the boiling point of the solvent used.
- a treating time is not restricted because phenoxyphosphazene compound is not adversely affected by contact with the adsorbent for a long time.
- the treating time is preferably between about 5 minutes to about 12 hours.
- the reagent or reactant for use in the present invention is at least one member selected from metal hydrides, hydrazine, hypochlorites, thiosulfates, dialkylsulfuric acids, ortho esters, diazoalkanes, lactones, alkanesultones, epoxy compounds and hydrogen peroxide.
- Examples of metal hydrides are lithium aluminum hydride, sodium borohydride and the like.
- Examples of hypochlorites are potassium hypochlorite, sodium hypochlorite and the like.
- Examples of thiosulfates are potassium thiosulfate, sodium thiosulfate and the like.
- Examples of dialkyl sulfuric acids are dimethyl sulfate, diethyl sulfate and the like.
- Examples of ortho esters are triethyl ortho acetate, triethyl ortho propionate and the like.
- Examples of diazoalkanes are diazomethane, diazoethane and the like.
- Examples of lactones are propiolactone, butyrolactone and the like.
- Examples of alkanesultones are 1,3-propanesultone, 1,4-butanesultone and the like.
- Examples of epoxy compounds are ethylene oxide, propylene oxide, butylene oxide and the like.
- hydrogen peroxide When used, it is usually used in the form of aqueous solution, having preferably a concentration of 1 to 30% by weight, more preferably a concentration of 5 to 20% by weight.
- Sodium borohydride is preferable as metal hydride; sodium hypochlorite is preferable as hypochlorite; sodium thiosulfate is preferable as thiosulfate; dimethyl sulfate is preferable as dialkyl sulfuric acid; triethyl ortho acetate is preferable as ortho ester; diazomethane is preferable as diazoalkane; 1,3-propanesultone ls preferable as alkanesultone.
- the amount of reagent used in the present invention may vary depending on the type of the reagents.
- a metal hydride is usually used in an amount of 0.5 to 100 parts by weight, preferably 1 to 50 parts by weight, based on 100 parts by weight of the phenoxyphosphazene compound to be treated.
- the reagent is a hypochlorite, it is usually used in an amount of 0.5 to 150 parts by weight, preferably 1 to 80 parts by weight, based on 100 parts by weight of the phenoxyphosphazene compound to be treated.
- the reagent When the reagent is a thiosulfate, it is usually used in an amount of 0.5 to 200 parts by weight, preferably about 1 to 100 parts by weight, based on 100 parts by weight of the phenoxyphosphazene compound to be treated.
- the reagent When the reagent is an alkanesultone, it is usually used in an amount of 0.01 to 50 parts by weight, preferably about 0.1 to 30 parts by weight, based on 100 parts by weight of the phenoxyphosphazene compound to be treated.
- the phenoxyphosphazene compound in a molten state may be stirred together with the reagent and then separated from the reagent.
- the phenoxyphosphazene compound is preferably dissolved and treated in an appropriate solvent.
- any solvent which can dissolve a phenoxyphosphazene compound and does not react with the reagent may be used.
- Useful solvents are those used in the above treatment by the adsorbent. Among these solvents, benzene, toluene, xylene and monochlorobenzene are preferable.
- the concentration of phenoxyphosphazene compound is not restricted. However, considering the ease of operation, the concentration is preferably 1 to 90% by weight, more preferably 5 to 80% by weight.
- the reaction temperature varies depending on the kind of reagents.
- the reaction temperature preferably ranges from about melting point of the phenoxyphosphazene compound to about 200° C.
- the treatement may be carried out at any temperature at which the solvent can dissolve the phenoxyphosphazene compound.
- the treatment is conducted at a temperature ranging from 0° C. to the boiling point of the solvent used.
- a treating time varies depending on the reagent. Generally, it is the range of about 5 minutes to about 12 hours.
- the two treatments mentioned above namely, the treatment with an adsorbent and the treatment with a reagent, may be carried out consecutively or simultaneously.
- Phenoxyphosphazene compounds to be treated according to the invention can be used in various forms.
- the reaction mixture produced by the reaction between a dichlorophosphazene compound and an alkali metal phenolate, etc. may be directly treated; the reaction mixture further diluted with an appropriate organic solvent as mentioned above may be treated; the phenoxyphosphazene compound isolated from the reaction mixture may be melted and treated; the isolated compound which is dissolved in an appropriate organic solvent may be treated; the phenoxyphosphazene compound which has been stored for a long time is melted or dissolved in an appropriate organic solvent and treated.
- the crosslinked phenoxyphosphazene compound (3) is preferably used.
- the acid value of the phenoxyphosphazene compound purified by the process of the invention is usually lower than 0.025, preferably lower than 0.020, more preferably lower than 0.015, even more preferably lower than 0.010, considering the influence thereof on properties of synthetic resins such as color change, reduced molecular weight, etc.
- the phenoxyphosphazene compound treated by the process of the invention is higher in purity and shows less coloration, a lower acid value, less weight loss on heating.
- the present invention provides a process for reducing the acid value of phenoxyphosphazene compound by treating the compound with at least one member selected from adsorbents and reagents.
- the phenoxyphosphazene compound treated by the process of the present invention can be advantageously used as a flame retardant.
- Synthetic resins to which the modified phenoxyphosphazene compound by the process of the invention can be added are not restricted, and may be any known thermoplastic resin or thermosetting resin.
- thermoplastic resins are polyethylene, polypropylene, polyisoprene, polyester (polyethylene terephthalate, polybutylene terephthalate, etc.), polybutadiene, polystyrene, high-impact polystyrene, acrylonitrile-styrene resin (AS resin), acrylonitrile-butadiene-styrene resin (ABS resin), methyl methacrylate-butadiene-styrene resin (MBS resin), methyl methacrylate-acrylonitrile-butadiene-styrene resin (MABS resin), acrylonitrile-acrylic rubber-styrene resin (AAS resin), polymethyl(meth)acrylate, polycarbonate, polyphenylene ether (PPE), modified polyphenylene ether, polyamide, polyphenylene sulfide, polyimide, polyether ether ketone, polysulfone, polyarylate, polyether ketone,
- Thermosetting resins include polyurethane, phenol resin, melamine resin, urea resin, unsatureated polyester resin, diallylphthalate resin, silicon resin, epoxy resin (bisphenol-A epoxy resin, bisphenol-F epoxy resin, bisphenol-AD epoxy resin, phenol novolac epoxy resin, cresol novolac epoxy resin, cyclic aliphatic epoxy resin, glycidyl ester epoxy resin, glycidyl amine epoxy resin, heterocyclic epoxy resin, urethane-modified epoxy resin, brominated bisphenol-A epoxy resin, etc.) and the like.
- epoxy resin bisphenol-A epoxy resin, bisphenol-F epoxy resin, bisphenol-AD epoxy resin, phenol novolac epoxy resin, cresol novolac epoxy resin, cyclic aliphatic epoxy resin, glycidyl ester epoxy resin, glycidyl amine epoxy resin, heterocyclic epoxy resin, urethane-modified epoxy resin, brominated bisphenol-A epoxy resin, etc.
- epoxy resin
- thermoplastic resins and thermosetting resins each may be used singly or in combinations of two or more species. At least one of thermoplastic resins and at least one of thermosetting resins are also used in combination as synthetic resins.
- the amount of the phenoxyphosphazene compound purified by the process of the invention is not restricted and can be suitably selected from a wide range depending on various conditions: the type of the synthetic resin to which the compound is added, presence of other additives, the type and amount of other additives, if used, the application of the desired resin composition, etc.
- the amount is usually about 0.1 to about 100 parts by weight, preferably about 0.5 to about 40 parts by weight, based on 100 parts by weight of a synthetic resin.
- the resin composition of the present invention may contain inorganic fillers, fluorocarbon resins, etc., to further enhance its flame retardancy, particularly its ability to prevent dripping (spread of flame caused by dripping of burning resins).
- Inorganic fillers and fluorocarbon resins may be used singly, or they may be used simultaneously.
- Inorganic fillers have the properties of improving the mechanical strength of resin compositions and enhancing prevention of dripping.
- Useful inorganic fillers can be selected from a wide range of resin fillers. Examples are mica, kaolin, talc, silica, clay, barium sulfate, barium carbonate, calcium carbonate, calcium sulfate, calcium silicate, titanium oxide, glass beads, glass balloon, glass flakes, fibrous alkali metal titanates (potassium titanate fibers, sodium titanate fibers, etc.), fibrous borates (aluminum borate fibers, magnesium borate fibers, etc.), zinc oxide fibers, titanium oxide fibers, magnesium oxide fibers, gypsum fibers, aluminum silicate fibers, calcium silicate fibers, silicon carbide fibers, titanium carbide fibers, silicon nitride fibers, titanium nitride fibers, carbon fibers, alumina fibers, alumina-silica fibers, zirconia fibers, quartz fibers, flaked titanate salts, flaked titanium dioxide and the like.
- Inorganic fillers may be used singly or in combinations of two or more species.
- the amount of inorganic fillers added is not restricted and is suitably selected from a wide range depending on various conditions: the type of resins added, the amount of a phenoxyphosphazene compound used, the type and amount of other additives used, the use of the resulting resin composition and the like. Considering the balance of the improvement of flame retardancy and the improvement of mechanical characteristics, the amount may be usually about 0.01 to about 50 parts by weight, preferably about 1 to about 20 parts by weight, based on 100 parts by weight of a synthetic resin.
- Known fluorocarbon resins can be used. Examples are polytetrafluoroethylene resin (PTFE), tetrafluoroethylene-hexafluoropropylene copolymer (FEP), tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer (PFA), tetrafluoroethylene-ethylene copolymer (ETFE), poly(trifluorochloroethylene) (CTFE), polyfluorovinylidene (PVdF), etc.
- PTFE polytetrafluoroethylene resin
- FEP tetrafluoroethylene-hexafluoropropylene copolymer
- PFA tetrafluoroethylene-perfluoroalkyl vinyl ether copolymer
- ETFE tetrafluoroethylene-ethylene copolymer
- CTFE poly(trifluorochloroethylene)
- PVdF polyfluorovinylidene
- Fluorocarbon resins may be used singly or in combinations of two or more species.
- the amount of fluorocarbon resins added is not restricted and is suitably selected from a wide range depending on various conditions: the type of the resin added, the amount of the phenoxyphosphazene compound used, the type and amount of other additives added, the use of the resulting resin composition, etc.
- the amount may be usually about 0.001 to about 20 parts by weight, preferably about 0.01 to about 5 parts by weight, based on 100 parts by weight of a synthetic resin.
- the resin composition of the present invention may further contain various flame retardants in an amount such that they do not deteriorate favorable properties of the resin composition.
- Known flame retardants are usable without any restriction. Examples are phosphazene compounds other than phenoxyphosphazene compounds, halogen-containing organic phosphorus compounds, halogen-free organic phosphorus compounds, inorganic flame retardants and the like. These may be used singly or in combinations of two or more species.
- the resin composition of the present invention may further contain general additives for resin in an amount such that they do not deteriorate favorable properties of the resin composition.
- additives for resin include, but are not limited to, ultraviolet absorbers (benzophenone type, benzotriazole type, cyanoacrylate type, etc.), photostabilizers (hindered amine type, etc.), antioxidants (hindered phenol type, organic phosphorus-type peroxide decomposers, organic sulfur-type peroxide decomposers, etc.), light screens (rutile-type titanium oxide, zinc oxide, chromium oxide, cerium oxide, etc.), metal deactivators (benzotriazole-type, etc.), optical quenching agents (organic nickel, etc.), anti-fogging agents, mildewproofing agents, antibacterial agents, pigments and the like.
- the flame-retardant resin composition of the present invention can be prepared by mixing and/or kneading a thermoplastic or thermosetting resin and a phenoxyphosphazene compound, and if needed one or more optional components such as an inorganic filler, a fluorocarbon resin, a flame retardant and or any other additive. These components can be used in a predetermined amount or a situationally appropriate amount, and the preparation can be carried out by any known method.
- a mixture of these components in the form of a powder, beads, flakes or pellets may be combined and/or mixed using a kneader such as a monoaxial extruder, a biaxial extruder or like extruder, a Banbury mixer, a pressure kneader, a two roll mill, etc.
- a kneader such as a monoaxial extruder, a biaxial extruder or like extruder, a Banbury mixer, a pressure kneader, a two roll mill, etc.
- the flame-retardant resin composition of the present invention can be formed into molded articles by a known method, for example, press molding, injection molding, extrusion molding, cast molding, etc.
- the resin composition can be molded into any shape such as single-layer or multilayer resin plates, sheets, films, balls, blocks, special shapes, etc.
- the flame-retardant resin composition of the present invention can find wide application in various fields where synthetic resins are usable: for example, electrical, electronics and telecommunication industries, precision machinery, automobiles and like transportation equipment, fiber products, manufacturing machinery, films for wrapping foods, food containers, products for use in agriculture, forestry and fishery, construction materials, medical goods, furniture parts, etc.
- Specific examples of electrical, electronics and telecommunication devices for which molded articles can be used include office and OA equipment such as printers, computers, word processors, keyboards, personal digital assistants (PDA), telephones, cellular phones, facsimile machines, copying machines, electronic cash registers (ECR), desk-top electronic calculators, electronic databooks, electronic dictionaries, cards, holders, stationery, etc.; electrical household appliances such as washing machines, refrigerators, vacuum cleaners, microwave ovens, lighting equipment, game machines, irons, kotatsu (low, covered table with a heat source underneath), etc.; audio-visual equipment such as TV, VTR, video cameras, radio cassette recorders, tape recorders, mini disc players, CD players, speakers, liquid crystal displays, etc.; and electric or electronic parts and telecommunication equipment, such as connectors, relays, condensers, switches, printed circuit boards materials, coil bobbins, semiconductor sealing materials, electric wires, cables, transformers, deflecting yokes, distribution boards, clocks, watches, etc.
- the flame-retardant resin moldings of the invention can be widely used for the following applications: materials for automobiles, vehicles, ships, aircraft and constructions, such as chairs, seats (e.g., padding, outer materials), belts, ceiling and wall covering, convertible tops, arm rests, door trims, rear package trays, carpets, mats, sun visors, wheel covers, mattress covers, air bags, insulation materials, hangers, hand straps, electric wire coating materials, electrical insulating materials, paints, coating materials, overlaying materials, floor materials, corner walls, carpets, wall papers, wall covering materials, exterior decorating materials, interior decorating materials, roofing materials, sound insulating panels, thermal insulation panels and window materials; and living necessities and sporting goods such as clothing, curtains, sheets, plywood, laminated fiber boards, carpets, entrance mats, seats, buckets, hoses, containers, glasses, bags, cases, goggles, skies, snowboards, skateboards, rackets, tents and musical instruments.
- materials for automobiles, vehicles, ships, aircraft and constructions such as
- the phenoxyphosphazene compound prepared by the process of the present invention is unlikely to adversely affect the hue (transparency, whiteness, etc.), heat resistance, weathering resistance, chemical resistance, etc., of the synthetic resin.
- the phenoxyphosphazene compound prepared by the process of the present invention prevents the polycarbonate resin from decomposition and a decrease in molecular weight, and hardly changes the hue or reduces mechanical characteristics such as impact resistance or other characteristics inherent in the resin such as heat resistance, molding processability, etc.
- a phenoxyphosphazene compound prepared by the process of the present invention has a higher quality, hydrolysis resistance, corrosion resistance, discoloration resistance, etc., and less odor than a phenoxyphosphazene compound washed with an aqueous solution containing an acid or an alkali.
- a resin composition prepared by adding the phenoxyphosphazene compound of the invention to a synthetic resin can endure severe long-term storage conditions and when molded does not corrode the molding device by which it is molded or cause other problems.
- the treatment of the present invention may efficiently remove or inactivate a trace amount of unreacted materials and impurities having phosphorus residues, amino groups or other groups, etc., which are formed by side reactions during the synthesis of the phenoxyphosphazene compound and adversely affect the properties of the synthetic resin.
- a 20% chlorobenzene solution (580 g) containing 1.0 unit mole (115.9 g) of dichlorophosphazene oligomers (a mixture of 72% of trimer, 17% of tetramer, 7% of pentamer and hexamer, 2% of heptamer and 2% of octamer and higher oligomers) was added dropwise to the toluene solution at 30° C. or lower with stirring, followed by reaction at 110° C. for 3 hours with stirring. To the reaction mixture was added the above prepared toluene solution of sodium phenolate with stirring, and the reaction was allowed to continue at 110° C. for 4 hours.
- dichlorophosphazene oligomers a mixture of 72% of trimer, 17% of tetramer, 7% of pentamer and hexamer, 2% of heptamer and 2% of octamer and higher oligomers
- the reaction mixture was washed three times with 1.0 liter of a 3% aqueous solution of sodium hydroxide and then three times with 1.0 liter of water.
- the toluene was distilled off under reduced pressure and the reaction mixture was heated and vacuum dried at 120° C. at a pressure of 4 hPa or less for 11 hours.
- To the solvent-free melt (211 g) was added 10 g of activated clay (trade name: Galleon Earth V2, a product of Mizusawa Industrial Chemicals, Ltd.). The mixture was stirred at 120° C. for 1 hour and heated and filtered to remove the activated clay. The filtrate was cooled, giving 208 g of a white solid.
- the crosslinked phenoxyphosphazene compound obtained above had an acid value of 0.008 mgKOH/g and a hydrolyzable chlorine content of 0.02%.
- the final product had a composition of [N ⁇ P(—O-p-Ph—O—) 0.15 (—O—Ph) 1.7 ], which was confirmed by measurement of phosphorus content and CHN elemental analysis.
- This product had a weight average molecular weight (Mw) of 1070 based on a polystyrene standard (GPC analysis). The product did not show a definite melting point and had a decomposition starting temperature of 308° C. and a 5% weight loss temperature of 313° C. as determined by TG/DTA analysis (thermogravimetric analysis).
- a polycarbonate resin (trade name: Tupilon S-2000F, manufactured by Mitsubishi Engineering Plastics Co., Ltd., the same product used below); 25 parts of an ABS resin (trade name: Santac UT-61, a product of Mitsui Chemicals Inc., the same product used below); 0.5 parts of polytetrafluoroethylene (PTFE, trade name; Fluon G307, a product of Asahi Glass Co., Ltd.); and 12.5 parts of the crosslinked phenoxyphosphazene compound obtained above were kneaded using a biaxial extruder and formed into pellets. The pellets were molded into disks with a diameter of 50 mm and a thickness of 1.4 mm using an injection molder.
- PTFE polytetrafluoroethylene
- a solvent-free melt was prepared in the same manner as in Example 1. The melt was then dissolved in a mixed solvent of 1.0 liter of tetrahydrofuran and 0.1 liter of methanol. After addition of 21 g of sodium borohydride, the mixture was stirred at room temperature for 24 hours.
- reaction mixture was neutralized with 2.5% hydrochloric acid and the organic layer was concentrated under reduced pressure.
- the solid was dissolved in 1.0 liter of toluene and washed twice with a 2.5% aqueous solution of sodium hydroxide, once with 2.5% hydrochloric acid, once with a 5% aqueous solution of sodium hydrogencarbonate, and twice with a 2% aqueous solution of sodium sulfate.
- the organic layer was concentrated under reduced pressure.
- the resulting product was heated and vacuum dried at 80° C. at a pressure of 4 hPa or less for 11 hours, giving 202 g of a white solid.
- the crosslinked phenoxyphosphazene compound obtained above had an acid value of 0.009 mgKOH/g and a hydrolyzable chlorine content of 0.02%.
- the final product had a composition of [N ⁇ P(—O-p-Ph—O—) 0.15 (—O—Ph) 1.7 ], which was confirmed by measurement of phosphorus content and CHN elemental analysis.
- This product had a weight average molecular weight (Mw) of 1070 based on a polystyrene standard (GPC analysis). The product did not show a definite melting point and had a decomposition starting temperature of 308° C. and a 5% weight loss temperature of 313° C. as determined by TG/DTA analysis.
- PC polycarbonate
- ABS resin Surge UT-61
- PTFE polycarbonate
- 12.5 parts of the crosslinked phenoxyphosphazene compound obtained above were kneaded using a biaxial extruder and formed into pellets.
- the pellets were molded into disks with a diameter of 50 mm and a thickness of 1.4 mm using an injection molder.
- a phenoxyphosphazene compound was prepared in the same manner as in Example 1 except that activated clay was not added after completion of the reaction. A slightly yellow solid (211 g) was obtained.
- the crosslinked phenoxyphosphazene compound thus obtained had an acid value of 0.039 mgKOH/g and a hydrolyzable chlorine content of 0.04%.
- the final product had a composition of [N ⁇ P(—O-p-Ph—O—) 0.15 (—O—Ph) 1.7 ], which was confirmed by measurement of phosphorus content and CHN elemental analysis.
- This product had a weight average molecular weight (Mw) of 1080 based on a polystyrene standard (GPC analysis). The product did not show a definite melting point and had a decomposition starting temperature of 306° C. and a 5% weight loss temperature of 311° C. as determined by TG/DTA analysis. The quantity of residual hydroxyl groups was found to be below the detection limit of the acetylation method.
- reaction mixture was concentrated to remove THF, and 1 liter of toluene was added to the concentrate.
- the resulting toluene solution was washed three times with 1 liter of a 2% aqueous solution of sodium hydroxide and then three times with 1 liter of water.
- the solution was passed through a column containing 50 g of activated alumina (a product of Wako Pure Chemical Industries, Ltd.) at room temperature.
- the resulting organic layer was concentrated under reduced pressure.
- the resulting product was heated and vacuum dried at 80° C. at a pressure of 4 hPa or less for 11 hours, giving 227 g of a white solid.
- the crosslinked phenoxyphosphazene compound thus obtained had an acid value of 0.007 mgKOH/g and a hydrolyzable chlorine content of 0.03%.
- This product had an approximate composition of [N ⁇ P(—O—Ph—C(CH 3 ) 2 —Ph—O—) 0.25 (—O—Ph) 1.50 ], which was confirmed by measurement of phosphorus content and CHN elemental analysis.
- This product had a weight average molecular weight (Mw) of 1120 based on a polystyrene standard (GPC analysis) .
- Mw weight average molecular weight
- the product did not show a definite melting point and had a decomposition starting temperature of 310° C. and a 5% weight loss temperature of 316° C. as determined by TG/DTA analysis.
- the quantity of residual hydroxyl groups was found to be below the detection limit of the acetylation method.
- a phenoxyphosphazene compound was prepared in the same manner as in Example 3 except for the following differences in the production process:
- the crosslinked phenoxyphosphazene compound thus obtained had an acid value of 0.008 mgKOH/g and a hydrolyzable chlorine content of 0.03%.
- the final product had a composition of [N ⁇ P(—O—Ph—C(CH 3 ) 2 —Ph—O—) 0.25 (—O—Ph) 1.50 ], which was confirmed by measurement of phosphorus content and CHN elemental analysis.
- This product had a weight average molecular weight (Mw) of 1120 based on a polystyrene standard (GPC analysis). The product did not show a definite melting point and had a decomposition starting temperature of 309° C. and a 5% weight loss temperature of 315° C. as determined by TG/DTA analysis.
- a phenoxyphosphazene compound was prepared in the same manner as in Example 3 except that activated alumina was not added after completion of the reaction. A slightly yellow solid (229 g) was obtained.
- the crosslinked phenoxyphosphazene compound thus obtained had an acid value of 0.035 mgKOH/g and a hydrolyzable chlorine content of 0.07%.
- the final product had a composition of [N ⁇ P(—O—Ph—C(CH 3 ) 2 —Ph—O—) 0.25 (—O—Ph) 1.50 ], which was confirmed by measurement of phosphorus content and CHN elemental analysis.
- This product had a weight average molecular weight (Mw) of 1130 based on a polystyrene standard (GPC analysis). The product did not show a definite melting point and had a decomposition starting temperature of 308° C. and a 5% weight loss temperature of 313° C. as determined by TG/DTA analysis. The quantity of residual hydroxyl groups was found to be below the detection limit of the acetylation method.
- This solution was added dropwise to 580 g of a 20% chlorobenzene solution containing 1.0 unit mole (115.9 g) of dichlorophosphazene oligomers (a mixture of 72% of trimer, 17% of tetramer, 7% of pentamer and hexamer, 2% of heptamer, 2% of octamer and higher oligomers) with cooling at 25° C. or lower and stirring, and the reaction was allowed to proceed at 71° C. to 73° C. for 5 hours. Then, the mixed solution A of sodium phenolate prepared above was added to the reaction mixture, and the reaction was allowed to continue at 71° C. to 73° C. for 3 hours.
- dichlorophosphazene oligomers a mixture of 72% of trimer, 17% of tetramer, 7% of pentamer and hexamer, 2% of heptamer, 2% of octamer and higher oli
- the reaction mixture was concentrated and dissolved again in 500 ml of chlorobenzene.
- the solution was washed three times with a 5% aqueous solution of sodium hydroxide, once with 5% sulfuric acid, once with a 5% aqueous solution of sodium bicarbonate and three times with water.
- 10 g of activated carbon (Carboraffin, a product of Takeda Chemical Industries, Ltd.) was added and stirred at room temperature for 1 hour.
- the activated carbon was separated by filtration and the organic layer was concentrated and dried, giving 216 g of a white solid.
- the crosslinked phenoxyphosphazene compound obtained above had an acid value of 0.006 mgKOH/g and a hydrolyzable chlorine content of 0.01% or less.
- This product had an approximate composition of [N ⁇ P(—O—Ph—SO 2 —Ph—O—) 0.05 (—O—Ph) 1.90 ], which was confirmed by measurement of phosphorus content and CHN elemental analysis.
- the product had a weight average molecular weight (Mw) of 1070 based on a polystyrene standard. This product had a melting point (Tm) of 106° C., a decomposition starting temperature of 323° C. and a 5% weight loss temperature of 337° C. as determined by TG/DTA analysis. The quantity of residual hydroxyl groups was below the detection limit of the acetylation method.
- Example 5 As in Example 5, the mixed solution B of sodium phenolate was added dropwise to the chlorobenzene solution containing dichlorophosphazene oligomers with cooling at 25° C. or lower and stirring, and the reaction was allowed to proceed at 71° C. to 73° C. with stirring for 5 hours. Then, the mixed solution A of sodium phenolate was added to the reaction mixture, and the reaction was allowed to continue at 71° C. to 73° C. for 3 hours.
- the crosslinked phenoxyphosphazene compound obtained above had an acid value of 0.008 mgKOH/g and a hydrolyzable chlorine content of 0.01% or less.
- This product had an approximate composition of [N ⁇ P(—O—Ph—SO 2 —Ph—O—) 0.05 (—O—Ph) 0.90 ], which was confirmed by measurement of phosphorus content and CHN elemental analysis.
- the product had a weight average molecular weight (Mw) of 1070 based on a polystyrene standard. This product had a melting point (Tm) of 106° C., a decomposition starting temperature of 322° C. and a 5% weight loss temperature of 337° C. as determined by TG/DTA analysis. The quantity of residual hydroxyl groups was found to be below the detection limit of the acetylation method.
- a phenoxyphosphazene compound was prepared in the same manner as in Example 5 except that activated carbon was not added after completion of the reaction. A light yellow solid (218 g) was obtained.
- the crosslinked phenoxyphosphazene compound obtained above had an acid value of 0.032 mgKOH/g and a hydrolyzable chlorine content of 0.01% or less.
- This product had an approximate composition of [N ⁇ P(—O—Ph—SO 2 —Ph—O—) 0.05 (—O—Ph) 1.90 ], which was confirmed by measurement of phosphorus content and CHN elemental analysis.
- the product had a weight average molecular weight (Mw) of 1080 based on a polystyrene standard. This product had a melting point (Tm) of 103° C., a decomposition starting temperature of 320° C. and a 5% weight loss temperature of 334° C. as determined by TG/DTA analysis. The quantity of residual hydroxyl groups was found to be below the detection limit of the acetylation method.
- the reaction mixture was concentrated and the concentrate was dissolved again in 500 ml of toluene. This solution was washed once with water, three times with a 5% aqueous solution of sodium hydroxide, once with 5% sulfuric acid, once with a 5% aqueous solution of sodium bicarbonate and once with water. Then 10 g of silica gel (trade name: Wako gel C-200, a product of Wako Pure Chemical Industries, Ltd.) was added to the toluene solution and the mixture was stirred at room temperature for 1 hour. After the silica gel was separated by filtration, the organic layer was concentrated under reduced pressure and the concentrate was heated and vacuum dried at 80° C. at a pressure of 4 hPa or less for 11 hours, giving 102 g of a white solid.
- silica gel trade name: Wako gel C-200, a product of Wako Pure Chemical Industries, Ltd.
- the crosslinked phenoxyphosphazene compound obtained above had an acid value of 0.010 mgKOH/g and a hydrolyzable chlorine content of 0.03% or less.
- This product had a melting point (Tm) of 109° C., a decomposition starting temperature of 326° C. and a 5% weight loss temperature of 340° C. as determined by TG/DTA analysis.
- Tm melting point
- the quantity of residual hydroxyl groups was found to be below the detection limit of the acetylation method.
- a phenoxyphosphazene compound was prepared in the same manner as in Example 7 except that silica gel was not added after completion of the reaction. A slightly yellow solid (109 g) was obtained.
- This crosslinked phenoxyphosphazene compound had an acid value of 0.045 mgKOH/g and a hydrolyzable chlorine content of 0.08%.
- This product had a melting point (Tm) of 107° C., a decomposition starting temperature of 324° C. and a 5% weight loss temperature of 338° C. as determined by TG/DTA analysis. The quantity of residual hydroxyl groups was found to be below the detection limit of the acetylation method.
- PTFE, PC resin and ABS resin are as described in Example 1.
- the other synthetic resins are as follows:
- PBT trade name “Torecon 1200S”, a product of Toray Industries, Inc.
- m-PPE trade name “Xyron X-9108”, a product of Asahi Kasei corporation.
- MFR Melt flow rate
- Condition 1 21.18N (2.16 kgf), 280° C.
- Condition 2 37.26N (3.80 kgf), 230° C.
- Condition 3 21.18N (2.16 kgf), 275° C.
- HDT Heat distortion temperature
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GB1013461A (en) * | 1961-11-23 | 1965-12-15 | Albright & Wilson Mfg Ltd | Novel phosphonitrilic compounds and preparation of polyurethanes therefrom |
US3996312A (en) * | 1974-11-21 | 1976-12-07 | Ethyl Corporation | Halophenoxyphosphazene fire retardants |
US4108805A (en) * | 1977-09-06 | 1978-08-22 | Armstrong Cork Company | Structurally regulated polyphosphazene copolymers |
US4551317A (en) * | 1981-10-26 | 1985-11-05 | Ethyl Corporation | Phosphonitrilic halide polymers |
US4440921A (en) * | 1982-06-21 | 1984-04-03 | Research Corporation | Coupling of polyorganophosphazenes to carboxylic acid |
JP3195485B2 (ja) * | 1993-12-27 | 2001-08-06 | 大塚化学株式会社 | 難燃剤組成物の製造方法及び難燃化方法 |
US5616768A (en) * | 1994-06-23 | 1997-04-01 | Daihachi Chemical Industry Co., Ltd. | Process for purifying phosphoric esters |
CA2275247C (en) * | 1997-10-15 | 2005-01-11 | Otsuka Chemical Co., Ltd. | Crosslinked phenoxyphosphazene compounds, flame retardant, flame-retardant resin compositions, and moldings of flame-retardant resins |
-
2000
- 2000-05-01 JP JP2000132114A patent/JP3389553B2/ja not_active Expired - Fee Related
-
2001
- 2001-04-26 KR KR10-2001-7016940A patent/KR100456261B1/ko not_active IP Right Cessation
- 2001-04-26 US US10/030,439 patent/US20030040643A1/en not_active Abandoned
- 2001-04-26 WO PCT/JP2001/003616 patent/WO2001083495A1/ja active Application Filing
- 2001-04-30 TW TW90110311A patent/TW575578B/zh not_active IP Right Cessation
-
2003
- 2003-12-23 US US10/745,255 patent/US6946578B2/en not_active Expired - Fee Related
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US20030176600A1 (en) * | 2000-09-04 | 2003-09-18 | Kazuo Yoshida | Polyphenylene ether resin composition |
US6825254B2 (en) * | 2000-09-04 | 2004-11-30 | Asahi Kasei Chemicals Corporation | Polyphenylene ether resin composition |
US20070040154A1 (en) * | 2003-11-07 | 2007-02-22 | Asahi Kasei Chemicals Corporation | Flame retarder composition |
DE112004002030B4 (de) * | 2003-11-07 | 2010-12-02 | Asahi Kasei Chemicals Corporation | Flammhemmende Zusammensetzung, flammhemmende Harzzusammensetzung und Formgegenstand |
US8562873B2 (en) | 2003-11-07 | 2013-10-22 | Asahi Kasei Chemicals Corporation | Flame retarder composition |
US20140079955A1 (en) * | 2010-06-03 | 2014-03-20 | Battelle Energy Alliance, Llc | An additive-resin admixture, methods of treating a wood product, a reaction product of an additive and a wood product, and a wood product |
US9637634B2 (en) | 2012-12-07 | 2017-05-02 | Covestro Deutschland Ag | Flame-retardant polycarbonate molding materials V |
WO2014086830A1 (de) * | 2012-12-07 | 2014-06-12 | Bayer Materialscience Ag | Flammgeschützte polycarbonatformmassen v |
WO2014086743A1 (de) | 2012-12-07 | 2014-06-12 | Bayer Materialscience Ag | Flammgeschützte polycarbonatformmassen i |
WO2014086832A1 (de) * | 2012-12-07 | 2014-06-12 | Bayer Materialscience Ag | Flammgeschützte polycarbonatformmassen iii |
CN104903394A (zh) * | 2012-12-07 | 2015-09-09 | 拜耳材料科技股份有限公司 | 防火的聚碳酸酯模塑料iii |
EP2928954A1 (de) * | 2012-12-07 | 2015-10-14 | Bayer Materialscience AG | Flammgeschützte polycarbonatformmassen ii |
US20140371360A1 (en) * | 2013-05-24 | 2014-12-18 | Sabic Global Technologies B.V. | Flame retardant polycarbonate compositions, methods of manufacture thereof and articles comprising the same |
US9346941B2 (en) * | 2013-12-27 | 2016-05-24 | Samsung Sdi Co., Ltd. | Polycarbonate resin composition having improved appearance and flowability |
US20150183958A1 (en) * | 2013-12-27 | 2015-07-02 | Samsung Sdi Co., Ltd. | Polycarbonate Resin Composition Having Improved Appearance and Flowability |
US20160319108A1 (en) * | 2015-04-30 | 2016-11-03 | Samsung Sdi Co., Ltd. | Polycarbonate Resin Composition and Molded Article Produced Therefrom |
US10125241B2 (en) * | 2015-04-30 | 2018-11-13 | Lotte Advanced Materials Co., Ltd. | Polycarbonate resin composition and molded article produced therefrom |
CN108822340A (zh) * | 2018-06-20 | 2018-11-16 | 上海工程技术大学 | 一种二氧化硅-碳-聚磷腈核壳型阻燃剂的制备方法 |
CN109608620A (zh) * | 2018-12-19 | 2019-04-12 | 北京化工大学 | 一种阻燃可降解的聚磷腈型环氧树脂及制备技术 |
WO2021228636A1 (en) | 2020-05-13 | 2021-11-18 | Covestro Deutschland Ag | Flame-retardant polycarbonate composition |
Also Published As
Publication number | Publication date |
---|---|
JP3389553B2 (ja) | 2003-03-24 |
KR100456261B1 (ko) | 2004-11-10 |
KR20020023242A (ko) | 2002-03-28 |
WO2001083495A1 (fr) | 2001-11-08 |
JP2001316396A (ja) | 2001-11-13 |
TW575578B (en) | 2004-02-11 |
US6946578B2 (en) | 2005-09-20 |
US20040127734A1 (en) | 2004-07-01 |
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