JPS5933136B2 - ペルオキシアルキルアリ−ル燐酸エステルから成る難燃剤 - Google Patents

ペルオキシアルキルアリ−ル燐酸エステルから成る難燃剤

Info

Publication number: JPS5933136B2
Authority: JP; Japan
Prior art keywords: group; phosphate; flame retardant; oxygen; raw material
Prior art date: 1978-01-03
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

Application number

JP15941478A

Other languages

English (en)

Japanese (ja)

Other versions

JPS54100440A (en

Inventor

ハリ−・ホイト・ビ−チヤム

ロバ−ト・ドナルド・ノ−リス

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

FMC Corp

Original Assignee

FMC Corp

Priority date (The priority date 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 date listed.)

1978-01-03

Filing date

1978-12-26

Publication date

1984-08-14

1978-12-26 Application filed by FMC Corp filed Critical FMC Corp

1979-08-08 Publication of JPS54100440A publication Critical patent/JPS54100440A/ja

1984-08-14 Publication of JPS5933136B2 publication Critical patent/JPS5933136B2/ja

Status Expired legal-status Critical Current

Links

-1 aryl phosphate ester Chemical class 0.000 title claims description 63
229910019142 PO4 Inorganic materials 0.000 title claims description 49
239000010452 phosphate Substances 0.000 title claims description 43
239000003063 flame retardant Substances 0.000 title claims description 18
RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims description 15
239000000203 mixture Substances 0.000 claims description 43
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 41
229910052760 oxygen Inorganic materials 0.000 claims description 40
239000001301 oxygen Substances 0.000 claims description 40
125000004437 phosphorous atom Chemical group 0.000 claims description 29
238000000034 method Methods 0.000 claims description 24
125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 23
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 22
150000002148 esters Chemical class 0.000 claims description 20
229910052698 phosphorus Inorganic materials 0.000 claims description 15
239000011574 phosphorus Substances 0.000 claims description 15
125000000217 alkyl group Chemical group 0.000 claims description 13
229910052799 carbon Inorganic materials 0.000 claims description 12
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
239000002994 raw material Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
239000007788 liquid Substances 0.000 claims description 6
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 6
229920003023 plastic Polymers 0.000 claims description 6
239000004033 plastic Substances 0.000 claims description 6
125000002877 alkyl aryl group Chemical group 0.000 claims description 5
MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 claims description 5
150000001721 carbon Chemical group 0.000 claims description 4
230000003647 oxidation Effects 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 2
229910052723 transition metal Inorganic materials 0.000 claims description 2
150000003624 transition metals Chemical class 0.000 claims description 2
235000021317 phosphate Nutrition 0.000 description 44
150000002978 peroxides Chemical class 0.000 description 33
238000004448 titration Methods 0.000 description 33
239000000047 product Substances 0.000 description 31
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 24
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 20
239000004280 Sodium formate Substances 0.000 description 19
235000019254 sodium formate Nutrition 0.000 description 19
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 17
239000000463 material Substances 0.000 description 16
SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 15
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
229920000642 polymer Polymers 0.000 description 13
239000000243 solution Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
238000002156 mixing Methods 0.000 description 12
150000003014 phosphoric acid esters Chemical class 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 10
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 9
150000003018 phosphorus compounds Chemical class 0.000 description 9
230000008569 process Effects 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000000654 additive Substances 0.000 description 8
239000004793 Polystyrene Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
229920002223 polystyrene Polymers 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000005502 peroxidation Methods 0.000 description 6
238000003860 storage Methods 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000004698 Polyethylene Substances 0.000 description 5
238000000354 decomposition reaction Methods 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
229920000573 polyethylene Polymers 0.000 description 5
239000004641 Diallyl-phthalate Substances 0.000 description 4
QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 4
238000001938 differential scanning calorimetry curve Methods 0.000 description 4
150000002432 hydroperoxides Chemical class 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
230000003244 pro-oxidative effect Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000011734 sodium Substances 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 4
235000019345 sodium thiosulphate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
230000000996 additive effect Effects 0.000 description 3
230000003078 antioxidant effect Effects 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
MPMSMUBQXQALQI-UHFFFAOYSA-N cobalt phthalocyanine Chemical compound [Co+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 MPMSMUBQXQALQI-UHFFFAOYSA-N 0.000 description 3
230000006835 compression Effects 0.000 description 3
238000007906 compression Methods 0.000 description 3
YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 3
238000000113 differential scanning calorimetry Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
239000012535 impurity Substances 0.000 description 3
229910052748 manganese Inorganic materials 0.000 description 3
239000011572 manganese Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
150000002903 organophosphorus compounds Chemical class 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
239000004014 plasticizer Substances 0.000 description 3
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
235000009518 sodium iodide Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
229910019213 POCl3 Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 2
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
239000004676 acrylonitrile butadiene styrene Substances 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
239000004305 biphenyl Substances 0.000 description 2
235000010290 biphenyl Nutrition 0.000 description 2
125000006267 biphenyl group Chemical group 0.000 description 2
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 2
238000007664 blowing Methods 0.000 description 2
230000003139 buffering effect Effects 0.000 description 2
230000000368 destabilizing effect Effects 0.000 description 2
JUHFQCKQQLMGAB-UHFFFAOYSA-N diphenyl (4-propan-2-ylphenyl) phosphate Chemical compound C1=CC(C(C)C)=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 JUHFQCKQQLMGAB-UHFFFAOYSA-N 0.000 description 2
229920001971 elastomer Polymers 0.000 description 2
238000007429 general method Methods 0.000 description 2
125000001867 hydroperoxy group Chemical group [*]OO[H] 0.000 description 2
230000006872 improvement Effects 0.000 description 2
230000006698 induction Effects 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
238000006317 isomerization reaction Methods 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
238000010992 reflux Methods 0.000 description 2
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 2
150000005846 sugar alcohols Polymers 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
229920006337 unsaturated polyester resin Polymers 0.000 description 2
238000005292 vacuum distillation Methods 0.000 description 2
UETPRJJVZPVPQI-UHFFFAOYSA-N (2-propan-2-ylphenyl) dihydrogen phosphate Chemical class CC(C)C1=CC=CC=C1OP(O)(O)=O UETPRJJVZPVPQI-UHFFFAOYSA-N 0.000 description 1
OLNXBQUOWIYBEV-UHFFFAOYSA-N (2-propan-2-ylphenyl)phosphonic acid Chemical compound CC(C)C1=CC=CC=C1P(O)(O)=O OLNXBQUOWIYBEV-UHFFFAOYSA-N 0.000 description 1
LSTPPRXYXIBZNL-UHFFFAOYSA-N 1-bis(4-propan-2-ylphenyl)phosphoryl-4-propan-2-ylbenzene Chemical compound C1=CC(C(C)C)=CC=C1P(=O)(C=1C=CC(=CC=1)C(C)C)C1=CC=C(C(C)C)C=C1 LSTPPRXYXIBZNL-UHFFFAOYSA-N 0.000 description 1
CPBBJYCJYCOYHG-UHFFFAOYSA-N 1-dimethylphosphoryl-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(P(C)(C)=O)C=C1 CPBBJYCJYCOYHG-UHFFFAOYSA-N 0.000 description 1
CHUGKEQJSLOLHL-UHFFFAOYSA-N 2,2-Bis(bromomethyl)propane-1,3-diol Chemical compound OCC(CO)(CBr)CBr CHUGKEQJSLOLHL-UHFFFAOYSA-N 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229920000178 Acrylic resin Polymers 0.000 description 1
239000004925 Acrylic resin Substances 0.000 description 1
229910000975 Carbon steel Inorganic materials 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
UUGLJVMIFJNVFH-UHFFFAOYSA-N Hexyl benzoate Chemical compound CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 1
229920004142 LEXAN™ Polymers 0.000 description 1
239000004418 Lexan Substances 0.000 description 1
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
229920000877 Melamine resin Polymers 0.000 description 1
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
239000004721 Polyphenylene oxide Substances 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
UGZICOVULPINFH-UHFFFAOYSA-N acetic acid;butanoic acid Chemical compound CC(O)=O.CCCC(O)=O UGZICOVULPINFH-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
238000013019 agitation Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229920003180 amino resin Polymers 0.000 description 1
229940069428 antacid Drugs 0.000 description 1
239000003159 antacid agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
QTPILKSJIOLICA-UHFFFAOYSA-N bis[hydroxy(phosphonooxy)phosphoryl] hydrogen phosphate Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(O)=O QTPILKSJIOLICA-UHFFFAOYSA-N 0.000 description 1
229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 1
SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
239000010962 carbon steel Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
229920006217 cellulose acetate butyrate Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
125000004965 chloroalkyl group Chemical group 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000002485 combustion reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000005336 cracking Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
238000001514 detection method Methods 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
JJXNVYMIYBNZQX-UHFFFAOYSA-N diphenyl (2-propan-2-ylphenyl) phosphate Chemical class CC(C)C1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 JJXNVYMIYBNZQX-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002085 enols Chemical class 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
238000007706 flame test Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000003709 fluoroalkyl group Chemical group 0.000 description 1
230000009477 glass transition Effects 0.000 description 1
229920000578 graft copolymer Polymers 0.000 description 1
239000005337 ground glass Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
UBIJTWDKTYCPMQ-UHFFFAOYSA-N hexachlorophosphazene Chemical compound ClP1(Cl)=NP(Cl)(Cl)=NP(Cl)(Cl)=N1 UBIJTWDKTYCPMQ-UHFFFAOYSA-N 0.000 description 1
229920005669 high impact polystyrene Polymers 0.000 description 1
239000004797 high-impact polystyrene Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
238000013508 migration Methods 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000000178 monomer Substances 0.000 description 1
150000004712 monophosphates Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
125000002081 peroxide group Chemical group 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
RMNODSGCFHVNDC-UHFFFAOYSA-N phenyl bis(2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C(C)C)OC1=CC=CC=C1 RMNODSGCFHVNDC-UHFFFAOYSA-N 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical class [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
150000003017 phosphorus Chemical class 0.000 description 1
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
238000010094 polymer processing Methods 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920006380 polyphenylene oxide Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000012545 processing Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000005060 rubber Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
238000009738 saturating Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229960005480 sodium caprylate Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
BYKRNSHANADUFY-UHFFFAOYSA-M sodium octanoate Chemical compound [Na+].CCCCCCCC([O-])=O BYKRNSHANADUFY-UHFFFAOYSA-M 0.000 description 1
PHVYLXNPRIDQCK-UHFFFAOYSA-M sodium;2-propan-2-ylphenolate Chemical compound [Na+].CC(C)C1=CC=CC=C1[O-] PHVYLXNPRIDQCK-UHFFFAOYSA-M 0.000 description 1
KQSJSRIUULBTSE-UHFFFAOYSA-M sodium;3-(3-ethylcyclopentyl)propanoate Chemical compound [Na+].CCC1CCC(CCC([O-])=O)C1 KQSJSRIUULBTSE-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
OBSZRRSYVTXPNB-UHFFFAOYSA-N tetraphosphorus Chemical compound P12P3P1P32 OBSZRRSYVTXPNB-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
238000001757 thermogravimetry curve Methods 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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 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
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/04—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polyesters
- C08F299/0442—Catalysts
- C08F299/045—Peroxy-compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Compositions Of Macromolecular Compounds (AREA)
Macromonomer-Based Addition Polymer (AREA)

JP15941478A 1978-01-03 1978-12-26 ペルオキシアルキルアリ−ル燐酸エステルから成る難燃剤 Expired JPS5933136B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US86649378A	1978-01-03	1978-01-03
US000000866493		1978-01-03

Publications (2)

Publication Number	Publication Date
JPS54100440A JPS54100440A (en)	1979-08-08
JPS5933136B2 true JPS5933136B2 (ja)	1984-08-14

Family

ID=25347731

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP15941478A Expired JPS5933136B2 (ja)	1978-01-03	1978-12-26	ペルオキシアルキルアリ−ル燐酸エステルから成る難燃剤

Country Status (6)

Country	Link
JP (1)	JPS5933136B2 (fr)
CA (1)	CA1120050A (fr)
DE (1)	DE2900149A1 (fr)
ES (1)	ES476540A1 (fr)
FR (1)	FR2413422A1 (fr)
GB (1)	GB2011419A (fr)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3725455A (en) *	1968-06-17	1973-04-03	Pennwalt Corp	Peroxy compounds containing a carbonate group
US3882203A (en) *	1972-09-25	1975-05-06	Texaco Belgium Nv Sa	Hydrocarbon-peroxy hydrocarbon phosphonates

1978
- 1978-12-15 CA CA000318071A patent/CA1120050A/fr not_active Expired
- 1978-12-26 JP JP15941478A patent/JPS5933136B2/ja not_active Expired
- 1978-12-29 GB GB7850253A patent/GB2011419A/en not_active Withdrawn
- 1978-12-29 FR FR7836868A patent/FR2413422A1/fr not_active Withdrawn
1979
- 1979-01-02 ES ES476540A patent/ES476540A1/es not_active Expired
- 1979-01-03 DE DE19792900149 patent/DE2900149A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
CA1120050A (fr)	1982-03-16
DE2900149A1 (de)	1979-08-16
JPS54100440A (en)	1979-08-08
ES476540A1 (es)	1979-11-16
FR2413422A1 (fr)	1979-07-27
GB2011419A (en)	1979-07-11

Publication	Publication Date	Title
TW445276B (en)	2001-07-11	Crosslinked phenoxyphosphazene compounds, process for the preparation thereof, flame retardants, flame-retardant resin compositions, and moldings of flame-retardant resins
JP5999775B2 (ja)	2016-09-28	リン含有混合物、それの製造方法及びそれの使用
KR20100097668A (ko)	2010-09-03	치환된 포스파젠 화합물 및 유기 중합체용 내연성 첨가제로서의 이의 용도
CN100453620C (zh)	2009-01-21	用于热塑性材料的阻燃性膦酸酯添加剂
WO2017119303A1 (fr)	2017-07-13	Composé organophosphoré et agent ignifuge le comprenant et procédé de production d'un composé organophosphoré
US5093494A (en)	1992-03-03	Flame retardants
EP0684250B1 (fr)	2000-09-27	Poly(pentaerythrityldiphosphonate) et son utilisation dans des compositions autoextinctrices
US4315082A (en)	1982-02-09	Phosphorus compounds
JPS5933136B2 (ja)	1984-08-14	ペルオキシアルキルアリ−ル燐酸エステルから成る難燃剤
WO2013058690A1 (fr)	2013-04-25	Nouveaux composés de phosphate à base de tétraoxaspiro[5.5]undécane et leur utilisation comme ignifugeants
US4067934A (en)	1978-01-10	Condensation products of phosphine oxides
US3250827A (en)	1966-05-10	Halogenated organic phosphonate esters
EP1210352B1 (fr)	2003-09-24	Formation de compositions organophosphorees oligomeriques presentant une meilleure couleur
GB2089350A (en)	1982-06-23	Flame retardant polymer compositions
EP0254683A2 (fr)	1988-01-27	Compositions retardatrices de flamme
JP2976246B2 (ja)	1999-11-10	リン化合物
EP0237135B1 (fr)	1992-11-25	Retardateur de flamme thermostable du type diphosphonate pour des matières plastiques
US3372209A (en)	1968-03-05	Diphosphorus ester hydrocarbon diols
GB1579036A (en)	1980-11-12	Cyclic phosphites and phosphates of polyalcohols their manufacture and their use
US4181646A (en)	1980-01-01	Phosphorus-containing flame retardant compositions
US3629367A (en)	1971-12-21	Fire-resistant polyester compositions
JPH03123757A (ja)	1991-05-27	安定剤としてのヒドロキシフェニルカルボン酸エステル
US4073829A (en)	1978-02-14	Phosphorus flame retardant compositions
CA1073470A (fr)	1980-03-11	Production d'oxydes d'hydroxyalkylphosphine
Cao et al.	2014	Simple synthesis of Biphosphonates with Excellent Flameproofing Properties