JPS6241674B2 - - Google Patents
Info
- Publication number
- JPS6241674B2 JPS6241674B2 JP57011901A JP1190182A JPS6241674B2 JP S6241674 B2 JPS6241674 B2 JP S6241674B2 JP 57011901 A JP57011901 A JP 57011901A JP 1190182 A JP1190182 A JP 1190182A JP S6241674 B2 JPS6241674 B2 JP S6241674B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- hydroxyl
- hydrogen
- composition according
- bromine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000000203 mixture Substances 0.000 claims abstract description 55
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 11
- 239000003063 flame retardant Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 7
- 239000003377 acid catalyst Substances 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 9
- 229920005989 resin Polymers 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 238000006266 etherification reaction Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 11
- 229910052794 bromium Inorganic materials 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000011342 resin composition Substances 0.000 claims 1
- -1 phosphine oxide ethers Chemical class 0.000 abstract description 16
- 238000006243 chemical reaction Methods 0.000 abstract description 13
- 239000011541 reaction mixture Substances 0.000 abstract description 12
- 239000000654 additive Substances 0.000 abstract description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000002170 ethers Chemical class 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003921 oil Substances 0.000 description 8
- 238000004809 thin layer chromatography Methods 0.000 description 8
- SZTDSGCADFWGKM-UHFFFAOYSA-N 3-[bis(3-hydroxypropyl)phosphoryl]propan-1-ol Chemical group OCCCP(=O)(CCCO)CCCO SZTDSGCADFWGKM-UHFFFAOYSA-N 0.000 description 7
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 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 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 4
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 229920001169 thermoplastic Polymers 0.000 description 4
- 239000004416 thermosoftening plastic Substances 0.000 description 4
- 239000004952 Polyamide Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229920002647 polyamide Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- YICAEXQYKBMDNH-UHFFFAOYSA-N 3-[bis(3-hydroxypropyl)phosphanyl]propan-1-ol Chemical compound OCCCP(CCCO)CCCO YICAEXQYKBMDNH-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- FGYHQFZISBDLDR-UHFFFAOYSA-N OCCC[PH2]=O Chemical compound OCCC[PH2]=O FGYHQFZISBDLDR-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- 229920006380 polyphenylene oxide Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical class [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004634 thermosetting polymer Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- SNZSAFILJOCMFM-UHFFFAOYSA-N 1-dipropylphosphorylpropane Chemical compound CCCP(=O)(CCC)CCC SNZSAFILJOCMFM-UHFFFAOYSA-N 0.000 description 1
- QWVCIORZLNBIIC-UHFFFAOYSA-N 2,3-dibromopropan-1-ol Chemical compound OCC(Br)CBr QWVCIORZLNBIIC-UHFFFAOYSA-N 0.000 description 1
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- QEJPOEGPNIVDMK-UHFFFAOYSA-N 3-bromo-2,2-bis(bromomethyl)propan-1-ol Chemical compound OCC(CBr)(CBr)CBr QEJPOEGPNIVDMK-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- MAHZBVJHJPWTPH-UHFFFAOYSA-N ClCC[PH2]=O Chemical compound ClCC[PH2]=O MAHZBVJHJPWTPH-UHFFFAOYSA-N 0.000 description 1
- AVCYPPTVQFMAGG-UHFFFAOYSA-N ClC[PH2]=O Chemical class ClC[PH2]=O AVCYPPTVQFMAGG-UHFFFAOYSA-N 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- BCVMCDJDUHGWCT-UHFFFAOYSA-N OCC[PH2]=O Chemical compound OCC[PH2]=O BCVMCDJDUHGWCT-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- VACOMSNNWGXHSF-UHFFFAOYSA-N chloro(dimethylphosphoryl)methane Chemical compound CP(C)(=O)CCl VACOMSNNWGXHSF-UHFFFAOYSA-N 0.000 description 1
- BHBRSNQBODBPND-UHFFFAOYSA-N chloro-[chloromethyl(methyl)phosphoryl]methane Chemical compound ClCP(=O)(C)CCl BHBRSNQBODBPND-UHFFFAOYSA-N 0.000 description 1
- NSRSKCIMAREEBU-UHFFFAOYSA-N chloromethylphosphane Chemical class PCCl NSRSKCIMAREEBU-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- WGMBWDBRVAKMOO-UHFFFAOYSA-L disodium;4-[2-(4-oxidophenyl)propan-2-yl]phenolate Chemical compound [Na+].[Na+].C=1C=C([O-])C=CC=1C(C)(C)C1=CC=C([O-])C=C1 WGMBWDBRVAKMOO-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5397—Phosphine oxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5304—Acyclic saturated phosphine oxides or thioxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Molecular Biology (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Polyethers (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20070885A JPS61251692A (ja) | 1982-01-29 | 1985-09-12 | 多官能性ホスフインオキサイドのオリゴマ−を含む混合エ−テル組成物とその製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/229,706 US4377653A (en) | 1981-01-30 | 1981-01-30 | Mixed ether compositions containing oligomers of polyfunctional phosphine oxides: flame retardants for polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57147544A JPS57147544A (en) | 1982-09-11 |
| JPS6241674B2 true JPS6241674B2 (enExample) | 1987-09-03 |
Family
ID=22862374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57011901A Granted JPS57147544A (en) | 1981-01-30 | 1982-01-29 | Mixed ether containing oligomers of multifunctional phosphine oxide and manufacture |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4377653A (enExample) |
| EP (1) | EP0057441B1 (enExample) |
| JP (1) | JPS57147544A (enExample) |
| AT (1) | ATE15488T1 (enExample) |
| AU (1) | AU7951982A (enExample) |
| BR (1) | BR8200473A (enExample) |
| CA (1) | CA1205244A (enExample) |
| DE (1) | DE3266084D1 (enExample) |
| ES (1) | ES509191A0 (enExample) |
| ZA (1) | ZA82609B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61251692A (ja) * | 1982-01-29 | 1986-11-08 | エフ エム シ− コ−ポレ−シヨン | 多官能性ホスフインオキサイドのオリゴマ−を含む混合エ−テル組成物とその製法 |
| US4552687A (en) * | 1983-07-08 | 1985-11-12 | Fmc Corporation | Electrically conductive plastics and production of same |
| FR2714060B1 (fr) * | 1993-12-20 | 1996-01-12 | Commissariat Energie Atomique | Dioxydes de diphosphines utilisables pour l'extraction des actinides et disels de phosphonium pour leur préparation. |
| JP2011506678A (ja) * | 2007-12-11 | 2011-03-03 | ダウ グローバル テクノロジーズ インコーポレイティド | 臭素化２−オキソ−１，３，２−ジオキサホスホリナン化合物を難燃添加剤として含有する押出ポリマー発泡体 |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2882321A (en) * | 1954-03-29 | 1959-04-14 | Searle & Co | Oxaalkane bisphosphonium compounds and the manufacture thereof |
| DE1098707B (de) * | 1958-10-04 | 1961-02-02 | Bayer Ag | Das Schuetzen der polymeren organischen Erzeugnisse gegen Entflammung |
| BE598179A (enExample) * | 1959-12-14 | |||
| US3213057A (en) * | 1960-12-06 | 1965-10-19 | Melpar Inc | Organo-phosphorus compounds |
| US3258492A (en) * | 1960-12-06 | 1966-06-28 | Melpar Inc | P-chloro or hydroxy benzyl tertiary phosphine oxides |
| US3267149A (en) * | 1962-07-13 | 1966-08-16 | Monsanto Res Corp | 4-hydroxybutyl phosphorus compounds |
| US3248429A (en) * | 1962-12-03 | 1966-04-26 | Hooker Chemical Corp | Phosphorus polymers |
| US3332962A (en) * | 1963-06-04 | 1967-07-25 | American Cyanamid Co | Phosphonium salts and derivatives and their preparation |
| US3333005A (en) * | 1963-06-04 | 1967-07-25 | American Cyanamid Co | Quaternary organophosphonium halides and preparation thereof |
| GB1065515A (en) * | 1964-01-13 | 1967-04-19 | Monsanto Co | Production of polyester compositions and shaped articles therefrom having an improved color |
| US3474981A (en) * | 1964-06-22 | 1969-10-28 | Clevite Corp | Record medium transport and rewind system for a recording instrument |
| DE1252413B (de) * | 1964-11-30 | 1967-10-19 | Chemische Fabrik Kalk GmbH Köln Kalk | Halogen- und phosphorhaltige organische Verbindungen als flammwidrigmachender Zusatz in Polyesterformmassen |
| US3404187A (en) * | 1965-03-10 | 1968-10-01 | Olin Mathieson | Ethers of hydroxyalkyl phosphine oxides and the preparation thereof |
| US3477953A (en) * | 1966-11-29 | 1969-11-11 | Hooker Chemical Corp | Sequestration of metal ions with hydroxyalkyl phosphine oxides |
| US3716580A (en) * | 1968-12-17 | 1973-02-13 | Monsanto Co | Functional tertiary phosphine oxides |
| US3732316A (en) * | 1970-11-12 | 1973-05-08 | Hooker Chemical Corp | Process for producing methyl phosphine oxides |
| US3779953A (en) * | 1971-08-16 | 1973-12-18 | Union Carbide Corp | Flame-retardant polyurethanes containing 1,2,5,6-tetrabromo-3,4-dihydroxyhexane |
| US3883476A (en) * | 1971-10-04 | 1975-05-13 | Ciba Geigy Corp | Pyromellitic diimides of 3,5-dialkyl-4-hydroxyphenylsubstituted amines |
| US3925303A (en) * | 1972-06-30 | 1975-12-09 | Rhone Poulenc Sa | Flameproofing of acrylonitrile polymers and copolymers |
| US3883474A (en) * | 1972-11-30 | 1975-05-13 | Hoechst Ag | Flame resistant thermoplastic polyesters |
| DE2258662A1 (de) * | 1972-11-30 | 1974-06-06 | Hoechst Ag | Neue tertiaere phosphinoxyde und verfahren zu ihrer herstellung |
| GB1506453A (en) * | 1975-03-11 | 1978-04-05 | Ici Ltd | Polymeric phosphonate esters and their use as flame-retardants for polymeric material |
| FR2333870A1 (fr) * | 1975-12-02 | 1977-07-01 | Pompey Acieries | Alliage refractaire a base de nickel et de chrome possedant une resistance elevee a l'oxydation, a la carburation et au fluage a tres haute temperature |
-
1981
- 1981-01-30 US US06/229,706 patent/US4377653A/en not_active Expired - Fee Related
-
1982
- 1982-01-14 AU AU79519/82A patent/AU7951982A/en not_active Abandoned
- 1982-01-18 CA CA000394383A patent/CA1205244A/en not_active Expired
- 1982-01-28 BR BR8200473A patent/BR8200473A/pt unknown
- 1982-01-29 DE DE8282100627T patent/DE3266084D1/de not_active Expired
- 1982-01-29 ES ES509191A patent/ES509191A0/es active Granted
- 1982-01-29 JP JP57011901A patent/JPS57147544A/ja active Granted
- 1982-01-29 EP EP82100627A patent/EP0057441B1/en not_active Expired
- 1982-01-29 AT AT82100627T patent/ATE15488T1/de active
- 1982-01-29 ZA ZA82609A patent/ZA82609B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE15488T1 (de) | 1985-09-15 |
| AU7951982A (en) | 1982-08-05 |
| ES8302043A1 (es) | 1982-12-16 |
| JPS57147544A (en) | 1982-09-11 |
| EP0057441A3 (en) | 1982-11-10 |
| CA1205244A (en) | 1986-05-27 |
| DE3266084D1 (en) | 1985-10-17 |
| ZA82609B (en) | 1982-12-29 |
| ES509191A0 (es) | 1982-12-16 |
| US4377653A (en) | 1983-03-22 |
| EP0057441B1 (en) | 1985-09-11 |
| BR8200473A (pt) | 1982-11-30 |
| EP0057441A2 (en) | 1982-08-11 |
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