CA1205244A - Mixed ether compositions containing oligomers of polyfunctional phosphine oxides and method for their manufacture - Google Patents
Mixed ether compositions containing oligomers of polyfunctional phosphine oxides and method for their manufactureInfo
- Publication number
- CA1205244A CA1205244A CA000394383A CA394383A CA1205244A CA 1205244 A CA1205244 A CA 1205244A CA 000394383 A CA000394383 A CA 000394383A CA 394383 A CA394383 A CA 394383A CA 1205244 A CA1205244 A CA 1205244A
- Authority
- CA
- Canada
- Prior art keywords
- mixed ether
- hydroxyl
- resin
- hydrogen
- radicals
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 239000000203 mixture Substances 0.000 title claims abstract description 50
- 238000000034 method Methods 0.000 title abstract description 7
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 title description 7
- -1 phosphine oxide ethers Chemical class 0.000 claims abstract description 33
- 239000003063 flame retardant Substances 0.000 claims abstract description 13
- 150000003254 radicals Chemical class 0.000 claims description 32
- 239000011347 resin Substances 0.000 claims description 30
- 229920005989 resin Polymers 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 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 8
- 239000004793 Polystyrene Substances 0.000 claims description 5
- 229920000265 Polyparaphenylene Polymers 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229920006122 polyamide resin Polymers 0.000 claims description 4
- 229920001707 polybutylene terephthalate Polymers 0.000 claims description 4
- 229920002223 polystyrene Polymers 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 10
- 229910052794 bromium Inorganic materials 0.000 claims 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 9
- 239000011342 resin composition Substances 0.000 claims 6
- 239000005020 polyethylene terephthalate Substances 0.000 claims 3
- 229920000139 polyethylene terephthalate Polymers 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000005846 sugar alcohols Polymers 0.000 claims 2
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 abstract description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 16
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract description 12
- 125000001931 aliphatic group Chemical group 0.000 abstract description 12
- 239000011541 reaction mixture Substances 0.000 abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 8
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract description 7
- 239000000654 additive Substances 0.000 abstract description 6
- 238000006243 chemical reaction Methods 0.000 abstract description 6
- 239000003377 acid catalyst Substances 0.000 abstract description 4
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 230000000996 additive effect Effects 0.000 abstract description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 150000001298 alcohols Chemical class 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
- 229960005419 nitrogen Drugs 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 238000006266 etherification reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229940059574 pentaerithrityl Drugs 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- SZTDSGCADFWGKM-UHFFFAOYSA-N 3-[bis(3-hydroxypropyl)phosphoryl]propan-1-ol Chemical group OCCCP(=O)(CCCO)CCCO SZTDSGCADFWGKM-UHFFFAOYSA-N 0.000 description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 3
- 239000004952 Polyamide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000011521 glass Substances 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
- 229920000570 polyether Polymers 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 2
- 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 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
- 229920002302 Nylon 6,6 Polymers 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 2
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 229960005150 glycerol Drugs 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 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 2
- 229940113165 trimethylolpropane Drugs 0.000 description 2
- 229940116269 uric acid Drugs 0.000 description 2
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
- SNZSAFILJOCMFM-UHFFFAOYSA-N 1-dipropylphosphorylpropane Chemical compound CCCP(=O)(CCC)CCC SNZSAFILJOCMFM-UHFFFAOYSA-N 0.000 description 1
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-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
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- YICAEXQYKBMDNH-UHFFFAOYSA-N 3-[bis(3-hydroxypropyl)phosphanyl]propan-1-ol Chemical compound OCCCP(CCCO)CCCO YICAEXQYKBMDNH-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
- 101100505076 Caenorhabditis elegans gly-2 gene Proteins 0.000 description 1
- MAHZBVJHJPWTPH-UHFFFAOYSA-N ClCC[PH2]=O Chemical class ClCC[PH2]=O MAHZBVJHJPWTPH-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- FGYHQFZISBDLDR-UHFFFAOYSA-N OCCC[PH2]=O Chemical compound OCCC[PH2]=O FGYHQFZISBDLDR-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 208000037062 Polyps Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- NSRSKCIMAREEBU-UHFFFAOYSA-N chloromethylphosphane Chemical class PCCl NSRSKCIMAREEBU-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical group CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 229940117969 neopentyl glycol Drugs 0.000 description 1
- 238000002103 osmometry Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000004437 phosphorous atom Chemical group 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
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229960003010 sodium sulfate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004634 thermosetting polymer Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005303 weighing Methods 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)
Applications Claiming Priority (2)
| 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 |
| US229,706 | 1981-01-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1205244A true CA1205244A (en) | 1986-05-27 |
Family
ID=22862374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000394383A Expired CA1205244A (en) | 1981-01-30 | 1982-01-18 | Mixed ether compositions containing oligomers of polyfunctional phosphine oxides and method for their 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 |
| 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 |
| JPS6241674B2 (enExample) | 1987-09-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO1999019383A1 (en) | Crosslinked phenoxyphosphazene compounds, flame retardant, flame-retardant resin compositions, and moldings of flame-retardant resins | |
| CN102171229A (zh) | 混合的二元醇聚膦酸酯化合物 | |
| CA1205244A (en) | Mixed ether compositions containing oligomers of polyfunctional phosphine oxides and method for their manufacture | |
| EP0275545A1 (de) | Phosphorhaltige Oligomere und Polymere mit Polyphenylenether-blöcken sowie Mischungen anderer Kunststoffe mit ihnen | |
| US3538196A (en) | Bis(oxypropylated pentaerythritol) oxypropylated pentaerythritol phosphonate | |
| US5530044A (en) | Alkyl end-capped, halogenated polyethers | |
| US2957856A (en) | Phosphorus-containing spirobi(metadioxane) resins | |
| US5837799A (en) | Fire-retardant compound, a process for producing said fire-retardant compound and a fire-retarded thermoplastic resin composition including said fire-retardant compound | |
| CA1190556A (en) | Aromatic bis (di-y-dioxaphosphorinane) compounds and polycarbonate compositions containing these compounds as thermal stabilizers | |
| US3419524A (en) | Polyphosphites as stabilizers for hydrocarbon polymers | |
| US3128259A (en) | Synthetic resins containing phenolic hydroxyl groups | |
| CA1133501A (en) | Diester of 3,5,3',5'-tetrabromo- bisphenol a with halogenated aromatic carboxylic acid | |
| EP0040665A1 (en) | Flame retardant polyphenylene oxide composition | |
| US3213057A (en) | Organo-phosphorus compounds | |
| EP0085201B1 (en) | Flame retardant polyphenylene ether-styrene thermoplastic resin compositions | |
| US3579470A (en) | Diphenyl oxide modified phenolic resin insulating varnishes | |
| GB1578359A (en) | Bromine containing oligomeric ethers | |
| US4065517A (en) | Flame retardant polysulfone composition | |
| EP0074345A1 (en) | Flame retardant polyphenylene ether-styrene thermoplastic resin compositions | |
| EP0244393B1 (en) | Flame retardant polyphenylene ether molding compositions | |
| US3093688A (en) | Process for preparing phenol dialcohols | |
| JP3054344B2 (ja) | 難燃剤組成物 | |
| EP0086760B1 (en) | Mixed phenyl/mesityl phosphate ester composition | |
| JPS61251692A (ja) | 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 | |
| US4357433A (en) | Flame retardant polyphenylene ether resin compositions |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 20030527 |