BRPI0711409A2 - isopropil fenil fosfatos com baixo teor de trifenilfosfato e alto teor de fósforo com alta orto alquilação - Google Patents
isopropil fenil fosfatos com baixo teor de trifenilfosfato e alto teor de fósforo com alta orto alquilação Download PDFInfo
- Publication number
- BRPI0711409A2 BRPI0711409A2 BRPI0711409-5A BRPI0711409A BRPI0711409A2 BR PI0711409 A2 BRPI0711409 A2 BR PI0711409A2 BR PI0711409 A BRPI0711409 A BR PI0711409A BR PI0711409 A2 BRPI0711409 A2 BR PI0711409A2
- Authority
- BR
- Brazil
- Prior art keywords
- alkylated
- triaryl phosphate
- phosphate ester
- weight
- alkylated triaryl
- Prior art date
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 20
- 239000011574 phosphorus Substances 0.000 title claims abstract description 20
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 230000029936 alkylation Effects 0.000 title abstract description 8
- 238000005804 alkylation reaction Methods 0.000 title abstract description 8
- WRXFONORSZHETC-UHFFFAOYSA-N phenyl propan-2-yl hydrogen phosphate Chemical class CC(C)OP(O)(=O)OC1=CC=CC=C1 WRXFONORSZHETC-UHFFFAOYSA-N 0.000 title 1
- -1 aryl phosphates Chemical class 0.000 claims abstract description 197
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 193
- 235000021317 phosphate Nutrition 0.000 claims abstract description 190
- 239000000203 mixture Substances 0.000 claims abstract description 130
- 238000000034 method Methods 0.000 claims abstract description 70
- 239000003063 flame retardant Substances 0.000 claims abstract description 30
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims abstract description 23
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 21
- 239000010452 phosphate Substances 0.000 claims description 164
- 238000006243 chemical reaction Methods 0.000 claims description 88
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 86
- 150000002989 phenols Chemical class 0.000 claims description 74
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 61
- 239000007795 chemical reaction product Substances 0.000 claims description 61
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 59
- 239000003054 catalyst Substances 0.000 claims description 58
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 claims description 39
- 239000000047 product Substances 0.000 claims description 32
- 150000003014 phosphoric acid esters Chemical class 0.000 claims description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 24
- 238000004821 distillation Methods 0.000 claims description 22
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 claims description 22
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical class C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 claims description 21
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 21
- 239000003085 diluting agent Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
- 239000007806 chemical reaction intermediate Substances 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000005233 alkylalcohol group Chemical group 0.000 claims description 11
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 10
- 239000004800 polyvinyl chloride Substances 0.000 claims description 10
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 9
- HPEUEJRPDGMIMY-IFQPEPLCSA-N molybdopterin Chemical compound O([C@H]1N2)[C@H](COP(O)(O)=O)C(S)=C(S)[C@@H]1NC1=C2N=C(N)NC1=O HPEUEJRPDGMIMY-IFQPEPLCSA-N 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 9
- 229920005830 Polyurethane Foam Polymers 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 239000011496 polyurethane foam Substances 0.000 claims description 8
- 229920001519 homopolymer Polymers 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000004604 Blowing Agent Substances 0.000 claims description 6
- 150000001298 alcohols Chemical class 0.000 claims description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- KEUMBYCOWGLRBQ-UHFFFAOYSA-N 2,4-di(propan-2-yl)phenol Chemical compound CC(C)C1=CC=C(O)C(C(C)C)=C1 KEUMBYCOWGLRBQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- NICHBOLLNPCHJH-UHFFFAOYSA-N dichloro phenyl phosphate Chemical class ClOP(=O)(OCl)OC1=CC=CC=C1 NICHBOLLNPCHJH-UHFFFAOYSA-N 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 239000003963 antioxidant agent Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 4
- 230000004907 flux Effects 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003077 polyols Chemical class 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 claims description 2
- 239000006057 Non-nutritive feed additive Substances 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000000956 alloy Substances 0.000 claims description 2
- 229910045601 alloy Inorganic materials 0.000 claims description 2
- 239000002216 antistatic agent Substances 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 239000007789 gas Substances 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 150000003230 pyrimidines Chemical class 0.000 claims description 2
- 150000003233 pyrroles Chemical class 0.000 claims description 2
- 239000012744 reinforcing agent Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical group 0.000 claims description 2
- 229920001169 thermoplastic Polymers 0.000 claims description 2
- JREYOWJEWZVAOR-UHFFFAOYSA-N triazanium;[3-methylbut-3-enoxy(oxido)phosphoryl] phosphate Chemical compound [NH4+].[NH4+].[NH4+].CC(=C)CCOP([O-])(=O)OP([O-])([O-])=O JREYOWJEWZVAOR-UHFFFAOYSA-N 0.000 claims 4
- 239000011342 resin composition Substances 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 229910001508 alkali metal halide Inorganic materials 0.000 claims 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims 1
- DWHGPUANDVSSDX-UHFFFAOYSA-N chloro phenyl hydrogen phosphate Chemical class ClOP(=O)(O)OC1=CC=CC=C1 DWHGPUANDVSSDX-UHFFFAOYSA-N 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- 150000004679 hydroxides Chemical class 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 abstract description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 131
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 32
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 26
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 26
- 238000005481 NMR spectroscopy Methods 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- 238000009472 formulation Methods 0.000 description 21
- 150000002148 esters Chemical class 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000006260 foam Substances 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- 230000008030 elimination Effects 0.000 description 15
- 238000003379 elimination reaction Methods 0.000 description 15
- 229920002635 polyurethane Polymers 0.000 description 15
- 239000004814 polyurethane Substances 0.000 description 15
- 229920000582 polyisocyanurate Polymers 0.000 description 14
- 239000011495 polyisocyanurate Substances 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- FPISENDBCQYRQB-UHFFFAOYSA-N phenol;phosphoric acid Chemical class OP(O)(O)=O.OC1=CC=CC=C1 FPISENDBCQYRQB-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- 229910019213 POCl3 Inorganic materials 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- 239000000376 reactant Substances 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 238000007792 addition Methods 0.000 description 9
- 230000003247 decreasing effect Effects 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- NUHSROFQTUXZQQ-UHFFFAOYSA-N isopentenyl diphosphate Chemical compound CC(=C)CCO[P@](O)(=O)OP(O)(O)=O NUHSROFQTUXZQQ-UHFFFAOYSA-N 0.000 description 7
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 6
- 239000013067 intermediate product Substances 0.000 description 6
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000523 sample Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- JJXNVYMIYBNZQX-UHFFFAOYSA-N diphenyl (2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 JJXNVYMIYBNZQX-UHFFFAOYSA-N 0.000 description 5
- 150000008282 halocarbons Chemical class 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003518 caustics Substances 0.000 description 4
- 238000005755 formation reaction Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 150000004714 phosphonium salts Chemical group 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 239000000538 analytical sample Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 235000013824 polyphenols Nutrition 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical group [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 3
- UETPRJJVZPVPQI-UHFFFAOYSA-N (2-propan-2-ylphenyl) dihydrogen phosphate Chemical compound CC(C)C1=CC=CC=C1OP(O)(O)=O UETPRJJVZPVPQI-UHFFFAOYSA-N 0.000 description 2
- GJVWMPQFNARTPN-UHFFFAOYSA-N (3-propan-2-ylphenyl) dihydrogen phosphate Chemical compound CC(C)C1=CC=CC(OP(O)(O)=O)=C1 GJVWMPQFNARTPN-UHFFFAOYSA-N 0.000 description 2
- JMEROBIHUFJHHG-UHFFFAOYSA-N (4-propan-2-ylphenyl) dihydrogen phosphate Chemical group CC(C)C1=CC=C(OP(O)(O)=O)C=C1 JMEROBIHUFJHHG-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- UWOKONWYYPRXCH-UHFFFAOYSA-N 1-[chloro-(2-propan-2-ylphenoxy)phosphoryl]oxy-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1OP(Cl)(=O)OC1=CC=CC=C1C(C)C UWOKONWYYPRXCH-UHFFFAOYSA-N 0.000 description 2
- BKMVKEHNEIKUMZ-UHFFFAOYSA-N 1-dichlorophosphoryloxy-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1OP(Cl)(Cl)=O BKMVKEHNEIKUMZ-UHFFFAOYSA-N 0.000 description 2
- VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241001582429 Tetracis Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
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- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
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- HVFKKINZIWVNQG-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)phenol Chemical compound CC(C)C1=CC(C(C)C)=C(O)C(C(C)C)=C1 HVFKKINZIWVNQG-UHFFFAOYSA-N 0.000 description 1
- ZDXGQHXSMPGQRI-UHFFFAOYSA-N 2,6-ditert-butyl-3-[(2,4-ditert-butyl-3-hydroxyphenyl)methyl]phenol Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC=C1CC1=CC=C(C(C)(C)C)C(O)=C1C(C)(C)C ZDXGQHXSMPGQRI-UHFFFAOYSA-N 0.000 description 1
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- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- LTTLGWXESLIUHQ-UHFFFAOYSA-N O(Cl)Cl.[F] Chemical compound O(Cl)Cl.[F] LTTLGWXESLIUHQ-UHFFFAOYSA-N 0.000 description 1
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- 239000004698 Polyethylene Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
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- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 229910010165 TiCu Inorganic materials 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- DZONBDFKZXLORJ-UHFFFAOYSA-N [2,4-di(propan-2-yl)phenyl] diphenyl phosphate Chemical compound CC(C)C1=CC(C(C)C)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 DZONBDFKZXLORJ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
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- QCMNWZDTWSLXMJ-UHFFFAOYSA-N diethylaminophosphanium;bromide Chemical compound [Br-].CCN([PH3+])CC QCMNWZDTWSLXMJ-UHFFFAOYSA-N 0.000 description 1
- PLBFTNYDDQQDME-UHFFFAOYSA-N diphenyl (3-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC(OP(=O)(OC=2C=CC=CC=2)OC=2C=CC=CC=2)=C1 PLBFTNYDDQQDME-UHFFFAOYSA-N 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 210000004124 hock Anatomy 0.000 description 1
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- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- KRPXAHXWPZLBKL-UHFFFAOYSA-L magnesium;diphenoxide Chemical compound [Mg+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 KRPXAHXWPZLBKL-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical group CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
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- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
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- 230000000865 phosphorylative effect Effects 0.000 description 1
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- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
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- 239000002952 polymeric resin Substances 0.000 description 1
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- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000006207 propylation Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
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Classifications
-
- 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
-
- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2101/00—Manufacture of cellular products
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
-
- 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
- C08K2201/00—Specific properties of additives
- C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
- Fireproofing Substances (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79478506P | 2006-04-24 | 2006-04-24 | |
| US60/794,785 | 2006-04-24 | ||
| US90829207P | 2007-03-27 | 2007-03-27 | |
| US90828707P | 2007-03-27 | 2007-03-27 | |
| US60/908,292 | 2007-03-27 | ||
| US60/908,287 | 2007-03-27 | ||
| PCT/US2007/067188 WO2007127691A2 (en) | 2006-04-24 | 2007-04-23 | Low triphenylphosphate, high phosphorous content isopropyl phenyl phosphates with high ortho alkylation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0711409A2 true BRPI0711409A2 (pt) | 2011-11-01 |
Family
ID=38610919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0711409-5A BRPI0711409A2 (pt) | 2006-04-24 | 2007-04-23 | isopropil fenil fosfatos com baixo teor de trifenilfosfato e alto teor de fósforo com alta orto alquilação |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8143433B2 (enExample) |
| EP (1) | EP2021347A2 (enExample) |
| JP (2) | JP2009534469A (enExample) |
| KR (1) | KR20080112323A (enExample) |
| AU (1) | AU2007244958A1 (enExample) |
| BR (1) | BRPI0711409A2 (enExample) |
| CA (1) | CA2649249A1 (enExample) |
| IL (1) | IL194529A0 (enExample) |
| MX (1) | MX2008013263A (enExample) |
| TW (1) | TW200745148A (enExample) |
| WO (1) | WO2007127691A2 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8143433B2 (en) * | 2006-04-24 | 2012-03-27 | Albemarle Corporation | Low triphenylphosphate, high phosphorous content isopropyl phenyl phosphates with high ortho alkylation |
| BRPI0814884A8 (pt) * | 2007-08-07 | 2015-09-22 | Albemarle Corp | espumas rígidas de poliuretano retardante de chamas e formulações de espuma rígida de poliuretano |
| EP2178962A2 (en) * | 2007-08-07 | 2010-04-28 | Albemarle Corporation | Flame retarded flexible polyurethane foams and flexible polyurethane foam formulations |
| TW201026763A (en) * | 2008-12-08 | 2010-07-16 | Albemarle Corp | Phosphorus flame retardants and applications therefor |
| US8747173B1 (en) | 2011-06-10 | 2014-06-10 | Hickory Springs Manufacturing Company | Flotation device |
| WO2014051312A1 (ko) * | 2012-09-26 | 2014-04-03 | Kwak Seung Min | 방향족 인산에스테르계 화합물을 포함한 방염제 및 그의 제조방법 |
| KR101241148B1 (ko) * | 2012-09-26 | 2013-03-11 | 곽승민 | 방향족 인산에스테르계 화합물을 포함한 방염제 및 그의 제조방법 |
| KR101302555B1 (ko) * | 2012-09-26 | 2013-09-02 | 곽승민 | 방향족 인산에스테르계 화합물을 포함한 방염제 및 그의 제조방법 |
| KR101354039B1 (ko) * | 2013-03-15 | 2014-01-23 | 곽승민 | 이중냉각장치 및 방향족 인산에스테르계 화합물의 합성장치 |
| JP6432935B2 (ja) * | 2014-11-20 | 2018-12-05 | アキレス株式会社 | 塩化ビニル系樹脂シート |
| CN105040154B (zh) * | 2015-07-22 | 2017-10-24 | 东华大学 | 一种阻燃聚酰胺66复合纤维及其制备方法 |
| EP3208276A1 (en) | 2016-02-18 | 2017-08-23 | PCC Rokita SA | Process for the preparation of a triaryl phosphate ester composition |
| US11339233B2 (en) * | 2017-09-15 | 2022-05-24 | Geon Performance Solutions, Llc | Flame retardant poly(vinyl chloride) compounds |
| RU2751888C1 (ru) * | 2020-10-29 | 2021-07-19 | Общество с ограниченной ответственностью Научно-производственное предприятие КВАЛИТЕТ ООО НПП КВАЛИТЕТ | Способ получения огнестойкой основы гидравлической жидкости |
| EP4431560A1 (de) * | 2023-03-15 | 2024-09-18 | LANXESS Deutschland GmbH | Phosphorsäureester-zusammensetzungen für flammwidriges weich-pvc mit hoher farbstabilität |
| US20250230177A1 (en) * | 2024-01-15 | 2025-07-17 | Polymer Additives, Inc. | Phosphate esters with very low triphenyl phosphate |
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| US4139487A (en) * | 1965-12-01 | 1979-02-13 | Albright & Wilson Limited | Mixed tri-aryl (phenyl and alkylphenyl) phosphate esters |
| GB1146173A (en) * | 1966-06-18 | 1969-03-19 | Geigy Uk Ltd | Production of triaryl phosphates |
| US4093680A (en) * | 1966-06-18 | 1978-06-06 | Ciba-Geigy Ag | Phosphorylated tertiary butylated phenol/phenol ester reaction mixtures |
| FR2118662A5 (en) | 1970-12-16 | 1972-07-28 | Monsanto Co | Alkyl aryl phosphate esters - for hydraulic fluids with high thermal stability and wide viscosity range |
| GB1414478A (en) | 1972-03-23 | 1975-11-19 | Albright & Wilson | Phosphorylation of alkylated phenols |
| US3859395A (en) * | 1973-10-09 | 1975-01-07 | Fmc Corp | Triaryl phosphate esters |
| GB2027712B (en) * | 1978-07-21 | 1983-03-23 | Ciba Geigy Ag | Triary phosphates |
| US4232359A (en) | 1979-04-09 | 1980-11-04 | Berkey-Colortran, Inc. | Spotlight or other illuminator |
| US4559184A (en) * | 1983-11-14 | 1985-12-17 | Stauffer Chemical Company | Phosphate ester synthesis without phosphorylation catalyst |
| EP0324716A3 (en) | 1988-01-12 | 1990-05-16 | Fmc Corporation (Uk) Limited | Triaryl phosphates |
| JP2999036B2 (ja) * | 1991-11-11 | 2000-01-17 | 本州化学工業株式会社 | アリールリン酸クロライド類の製造方法 |
| US5206404A (en) * | 1992-04-27 | 1993-04-27 | Fmc Corporation | Triaryl phosphate ester composition and process for its preparation |
| US5457139A (en) | 1993-07-26 | 1995-10-10 | Monsanto Company | Flexible water-blown polyurethane foams |
| US5302303A (en) * | 1993-08-24 | 1994-04-12 | Miles Inc. | Storage stable isocyanate-reactive compositions for use in flame-retardent systems |
| GB9722719D0 (en) * | 1997-10-29 | 1997-12-24 | Fmc Corp Uk Ltd | Production of phosphate esters |
| US6242631B1 (en) * | 1998-09-21 | 2001-06-05 | Akzo Nobel Nv | Triaryl phosphate ester composition |
| WO2000017210A1 (en) | 1998-09-21 | 2000-03-30 | Akzo Nobel N.V. | Triaryl phosphate ester composition |
| US8143433B2 (en) * | 2006-04-24 | 2012-03-27 | Albemarle Corporation | Low triphenylphosphate, high phosphorous content isopropyl phenyl phosphates with high ortho alkylation |
-
2007
- 2007-04-23 US US12/297,273 patent/US8143433B2/en not_active Expired - Fee Related
- 2007-04-23 MX MX2008013263A patent/MX2008013263A/es active IP Right Grant
- 2007-04-23 BR BRPI0711409-5A patent/BRPI0711409A2/pt not_active IP Right Cessation
- 2007-04-23 CA CA002649249A patent/CA2649249A1/en not_active Abandoned
- 2007-04-23 WO PCT/US2007/067188 patent/WO2007127691A2/en not_active Ceased
- 2007-04-23 KR KR1020087025850A patent/KR20080112323A/ko not_active Ceased
- 2007-04-23 AU AU2007244958A patent/AU2007244958A1/en not_active Abandoned
- 2007-04-23 TW TW096114184A patent/TW200745148A/zh unknown
- 2007-04-23 EP EP07797267A patent/EP2021347A2/en not_active Withdrawn
- 2007-04-23 JP JP2009507914A patent/JP2009534469A/ja active Pending
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2008
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2011
- 2011-09-14 US US13/232,388 patent/US8350074B2/en not_active Expired - Fee Related
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2013
- 2013-04-12 JP JP2013083876A patent/JP2013151552A/ja active Pending
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|---|---|
| US20120004438A1 (en) | 2012-01-05 |
| JP2013151552A (ja) | 2013-08-08 |
| WO2007127691A3 (en) | 2008-01-03 |
| WO2007127691A2 (en) | 2007-11-08 |
| IL194529A0 (en) | 2009-08-03 |
| MX2008013263A (es) | 2008-10-27 |
| EP2021347A2 (en) | 2009-02-11 |
| AU2007244958A1 (en) | 2007-11-08 |
| JP2009534469A (ja) | 2009-09-24 |
| US8143433B2 (en) | 2012-03-27 |
| US8350074B2 (en) | 2013-01-08 |
| TW200745148A (en) | 2007-12-16 |
| CA2649249A1 (en) | 2007-11-08 |
| KR20080112323A (ko) | 2008-12-24 |
| US20100012906A1 (en) | 2010-01-21 |
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