CA1054282A - Halogen containing fire retardant additive with improved heat stability - Google Patents
Halogen containing fire retardant additive with improved heat stabilityInfo
- Publication number
- CA1054282A CA1054282A CA221,052A CA221052A CA1054282A CA 1054282 A CA1054282 A CA 1054282A CA 221052 A CA221052 A CA 221052A CA 1054282 A CA1054282 A CA 1054282A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- weight
- parts
- polymer
- percent
- 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
- 239000003063 flame retardant Substances 0.000 title claims abstract description 24
- 229910052736 halogen Inorganic materials 0.000 title claims description 15
- 150000002367 halogens Chemical class 0.000 title claims description 10
- 239000000654 additive Substances 0.000 title abstract description 24
- 230000000996 additive effect Effects 0.000 title description 11
- 239000000203 mixture Substances 0.000 claims abstract description 118
- 229920000642 polymer Polymers 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 21
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- -1 polyethylene terephthalate Polymers 0.000 claims description 13
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 10
- 229920005669 high impact polystyrene Polymers 0.000 claims description 8
- 239000004797 high-impact polystyrene Substances 0.000 claims description 8
- 239000004793 Polystyrene Substances 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 7
- 229920002223 polystyrene Polymers 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 6
- 229920000647 polyepoxide Polymers 0.000 claims description 5
- 239000011787 zinc oxide Substances 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000004698 Polyethylene Substances 0.000 claims description 4
- 239000004743 Polypropylene Substances 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000004677 Nylon Substances 0.000 claims description 3
- 239000005062 Polybutadiene Substances 0.000 claims description 3
- 239000002174 Styrene-butadiene Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229920001778 nylon Polymers 0.000 claims description 3
- 229920002857 polybutadiene Polymers 0.000 claims description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052787 antimony Inorganic materials 0.000 claims description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052797 bismuth Inorganic materials 0.000 claims description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052785 arsenic Inorganic materials 0.000 claims 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
- 229910000765 intermetallic Inorganic materials 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229920000139 polyethylene terephthalate Polymers 0.000 claims 1
- 239000005020 polyethylene terephthalate Substances 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000011115 styrene butadiene Substances 0.000 claims 1
- 150000002848 norbornenes Chemical class 0.000 abstract description 4
- 238000005698 Diels-Alder reaction Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 41
- 238000000465 moulding Methods 0.000 description 26
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
- 238000005658 halogenation reaction Methods 0.000 description 14
- 229910052760 oxygen Inorganic materials 0.000 description 14
- 239000001301 oxygen Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 13
- 230000026030 halogenation Effects 0.000 description 13
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 13
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 13
- 239000000376 reactant Substances 0.000 description 12
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
- 230000031709 bromination Effects 0.000 description 6
- 238000005893 bromination reaction Methods 0.000 description 6
- 230000002140 halogenating effect Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- GVYLCNUFSHDAAW-UHFFFAOYSA-N mirex Chemical compound ClC12C(Cl)(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C4(Cl)C1(Cl)Cl GVYLCNUFSHDAAW-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 3
- 238000006731 degradation reaction Methods 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 125000003518 norbornenyl group Polymers C12(C=CC(CC1)C2)* 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- ZBBLRPRYYSJUCZ-GRHBHMESSA-L (z)-but-2-enedioate;dibutyltin(2+) Chemical class [O-]C(=O)\C=C/C([O-])=O.CCCC[Sn+2]CCCC ZBBLRPRYYSJUCZ-GRHBHMESSA-L 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- RLKOAZNVJZJJFB-UHFFFAOYSA-N 1,2,3,4-tetrachlorocyclopenta-1,3-diene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C1 RLKOAZNVJZJJFB-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- NHYCGSASNAIGLD-UHFFFAOYSA-N Chlorine monoxide Chemical compound Cl[O] NHYCGSASNAIGLD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 241001163743 Perlodes Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 229920002903 fire-safe polymer Polymers 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000009533 lab test Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011369 resultant mixture Substances 0.000 description 2
- 229920001169 thermoplastic Polymers 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 2
- PHYHWKJTYWPNCS-PDPXOMPHSA-N (1R,4S,5R)-1,2,3,4,7,7-hexachloro-5-(2,3,4,5-tetrabromophenyl)bicyclo[2.2.1]hept-2-ene Chemical compound ClC1=C(Cl)[C@@]2(Cl)[C@H](C[C@]1(Cl)C2(Cl)Cl)C1=C(Br)C(Br)=C(Br)C(Br)=C1 PHYHWKJTYWPNCS-PDPXOMPHSA-N 0.000 description 1
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 1
- NUYUCYZVFLZIPX-UHFFFAOYSA-N 1,2,3,4,5,5-hexabromocyclopenta-1,3-diene Chemical compound BrC1=C(Br)C(Br)(Br)C(Br)=C1Br NUYUCYZVFLZIPX-UHFFFAOYSA-N 0.000 description 1
- BDTKCOREDQRWGK-UHFFFAOYSA-N 1,2,3,4,5,5-hexafluorocyclopenta-1,3-diene Chemical compound FC1=C(F)C(F)(F)C(F)=C1F BDTKCOREDQRWGK-UHFFFAOYSA-N 0.000 description 1
- UKKNLZIOJGGOSG-UHFFFAOYSA-N 1,2,3,4,5-pentachloro-5-methylcyclopenta-1,3-diene Chemical compound CC1(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl UKKNLZIOJGGOSG-UHFFFAOYSA-N 0.000 description 1
- KEACIABIOKOFBJ-UHFFFAOYSA-N 1,2,3,4,5-pentafluorocyclopenta-1,3-diene Chemical compound FC1C(F)=C(F)C(F)=C1F KEACIABIOKOFBJ-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- ZITVKGIRQCDOSX-UHFFFAOYSA-N 1h-cyclopropa[a]naphthalene Chemical compound C1=CC=CC2=C3CC3=CC=C21 ZITVKGIRQCDOSX-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- 229920008128 Ameripol Polymers 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical class C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- UUPWEGAONCOIFJ-UHFFFAOYSA-N CCCCC(CC)COC(=O)OOC(O)=O Chemical compound CCCCC(CC)COC(=O)OOC(O)=O UUPWEGAONCOIFJ-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- WHTNHYRHHHFFBV-UHFFFAOYSA-N ClNS(=O)=O Chemical compound ClNS(=O)=O WHTNHYRHHHFFBV-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- QBYJBZPUGVGKQQ-UHFFFAOYSA-N aldrin Chemical compound C1C2C=CC1C1C(C3(Cl)Cl)(Cl)C(Cl)=C(Cl)C3(Cl)C12 QBYJBZPUGVGKQQ-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- ZHNUHDYFZUAESO-OUBTZVSYSA-N aminoformaldehyde Chemical compound N[13CH]=O ZHNUHDYFZUAESO-OUBTZVSYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001495 arsenic compounds Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000011790 ferrous sulphate Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 229940093920 gynecological arsenic compound Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- KSRHWBLHVZJTKV-UHFFFAOYSA-N iodobenzene dichloride Chemical compound ClI(Cl)C1=CC=CC=C1 KSRHWBLHVZJTKV-UHFFFAOYSA-N 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 125000006682 monohaloalkyl group Chemical group 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002846 norbornadienes Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- RYFZYYUIAZYQLC-UHFFFAOYSA-N perchloromethyl mercaptan Chemical compound ClSC(Cl)(Cl)Cl RYFZYYUIAZYQLC-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000004184 polymer manufacturing process Methods 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920005606 polypropylene copolymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000007347 radical substitution reaction Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- IODUDVQDMKBOJC-UHFFFAOYSA-N tert-butyl hypobromite Chemical compound CC(C)(C)OBr IODUDVQDMKBOJC-UHFFFAOYSA-N 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- XPDICGYEJXYUDW-UHFFFAOYSA-N tetraarsenic tetrasulfide Chemical compound S1[As]2S[As]3[As]1S[As]2S3 XPDICGYEJXYUDW-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- JXIODIIPBVDVBP-UHFFFAOYSA-N trichloromethanesulfonyl bromide Chemical compound ClC(Cl)(Cl)S(Br)(=O)=O JXIODIIPBVDVBP-UHFFFAOYSA-N 0.000 description 1
- ZCPSWAFANXCCOT-UHFFFAOYSA-N trichloromethanesulfonyl chloride Chemical compound ClC(Cl)(Cl)S(Cl)(=O)=O ZCPSWAFANXCCOT-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene 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
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing 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
- C08K5/02—Halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/447,807 US3941758A (en) | 1974-03-04 | 1974-03-04 | Halogen containing fire retardant additive with improved heat stability |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1054282A true CA1054282A (en) | 1979-05-08 |
Family
ID=23777840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA221,052A Expired CA1054282A (en) | 1974-03-04 | 1975-02-24 | Halogen containing fire retardant additive with improved heat stability |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US3941758A (en, 2012) |
| JP (1) | JPS50121342A (en, 2012) |
| BE (1) | BE826165A (en, 2012) |
| CA (1) | CA1054282A (en, 2012) |
| DE (1) | DE2508097A1 (en, 2012) |
| FR (1) | FR2263273B1 (en, 2012) |
| GB (1) | GB1484441A (en, 2012) |
| IT (1) | IT1033260B (en, 2012) |
| NL (1) | NL7502422A (en, 2012) |
| SE (1) | SE7502349L (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4421890A (en) * | 1973-09-26 | 1983-12-20 | General Electric Company | Fire retarding system for polymeric compositions, and a method and products comprising the same |
| US4155949A (en) * | 1975-01-21 | 1979-05-22 | Mitsubishi Gas Chemical Company, Inc. | Fire retardant polycarbonate resin composition |
| EP0004175A1 (en) * | 1978-03-13 | 1979-09-19 | Uniroyal, Inc. | Smoke retarded polymers and method for preparing them |
| CH642670A5 (de) | 1979-12-21 | 1984-04-30 | Ciba Geigy Ag | Verfahren zur herstellung von vernetzten kunststoffen und ihre verwendung. |
| US4567214A (en) * | 1984-09-14 | 1986-01-28 | Occidental Chemical Corporation | Flame retardant polyolefin compositions |
| US5194482A (en) * | 1990-08-23 | 1993-03-16 | Ferro Corporation | Flame retardant resin composition containing styrenic polymers |
| AU8534591A (en) * | 1990-08-23 | 1992-03-17 | Ferro Corporation | Improved flame retardant resin composition containing styrenic polymers |
| US20090234053A1 (en) * | 2008-03-14 | 2009-09-17 | Zeynep Ergungor | Copper containing polyester-polyamide compositions |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2519190A (en) * | 1946-01-26 | 1950-08-15 | Velsicol Corp | Polyhalogenated polycyclic hydrocarbons and insecticides thereof |
| US2640000A (en) * | 1947-06-07 | 1953-05-26 | Diamond Alkali Co | Flameproofing method and product |
| US2610920A (en) * | 1948-11-01 | 1952-09-16 | Hopkinson Harry | Flameproofing composition |
| US2676131A (en) * | 1948-12-04 | 1954-04-20 | Shell Dev | Halogenated heterocyclic insect toxicants |
| US2717851A (en) * | 1950-04-18 | 1955-09-13 | Shell Dev | Polycyclic insecticidal compounds |
| US2760947A (en) * | 1953-02-24 | 1956-08-28 | Dow Chemical Co | Self-extinguishing alkenyl polymer compositions containing bromochloro compounds |
| US2955141A (en) * | 1958-01-31 | 1960-10-04 | Universal Oil Prod Co | Condensation of polyhalocycloalkadienes with non-conjugated cycloalkadienes |
| NL293800A (en, 2012) * | 1962-06-08 | |||
| US3331797A (en) * | 1962-06-11 | 1967-07-18 | Huels Chemische Werke Ag | Flame-resistant polyolefine compositions |
| US3347822A (en) * | 1962-11-12 | 1967-10-17 | Kalk Chemische Fabrik Gmbh | Flameproofed synthetic resins |
| GB1090598A (en) * | 1964-08-17 | 1967-11-08 | Hooker Chemical Corp | Polymers and coatings rendered flame retardant by the addition of halogenated cyclopentadiene diels-alder adducts |
| DE1244395B (de) * | 1965-08-25 | 1967-07-13 | Basf Ag | Formmassen zur Herstellung selbstverloeschender Formkoerper |
| US3658634A (en) * | 1970-08-20 | 1972-04-25 | Toray Industries | Fire-retardant sheath and core type conjugate fiber |
| US3828003A (en) * | 1970-10-26 | 1974-08-06 | Nippon Oils & Fats Co Ltd | Flame resistant polymer compositions |
| ZA718662B (en) | 1971-02-12 | 1972-09-27 | Cities Service Co | Fire retardant compositions |
| US3730929A (en) * | 1971-04-30 | 1973-05-01 | Cities Service Co | Bloom inhibited flame retardant compositions |
| US3787356A (en) * | 1972-05-08 | 1974-01-22 | Velsicol Chemical Corp | Fire retardant compositions |
| US3899463A (en) * | 1972-08-18 | 1975-08-12 | Cities Service Co | Flame-retardant composition |
| US3950456A (en) * | 1972-08-18 | 1976-04-13 | Cities Service Company | Flame-retardant composition |
| US3794614A (en) * | 1972-11-29 | 1974-02-26 | Cities Service Co | Flame retardant propylene polymers |
| US3888820A (en) * | 1972-12-20 | 1975-06-10 | Universal Oil Prod Co | Novel flame retardant compositions of matter |
| US3940355A (en) * | 1973-11-01 | 1976-02-24 | Kellwood Company | Composition and method for imparting fire resistance and water repellency to fabric |
-
1974
- 1974-03-04 US US05/447,807 patent/US3941758A/en not_active Expired - Lifetime
-
1975
- 1975-02-24 CA CA221,052A patent/CA1054282A/en not_active Expired
- 1975-02-25 DE DE19752508097 patent/DE2508097A1/de active Pending
- 1975-02-26 JP JP50023792A patent/JPS50121342A/ja active Pending
- 1975-02-27 IT IT20731/75A patent/IT1033260B/it active
- 1975-02-28 NL NL7502422A patent/NL7502422A/xx unknown
- 1975-02-28 BE BE153902A patent/BE826165A/xx unknown
- 1975-03-03 GB GB8798/75A patent/GB1484441A/en not_active Expired
- 1975-03-03 SE SE7502349A patent/SE7502349L/xx unknown
- 1975-03-04 FR FR7506754A patent/FR2263273B1/fr not_active Expired
-
1976
- 1976-02-02 US US05/654,244 patent/US4098761A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2263273B1 (en, 2012) | 1977-04-15 |
| FR2263273A1 (en, 2012) | 1975-10-03 |
| SE7502349L (en, 2012) | 1975-09-05 |
| US3941758A (en) | 1976-03-02 |
| JPS50121342A (en, 2012) | 1975-09-23 |
| GB1484441A (en) | 1977-09-01 |
| BE826165A (fr) | 1975-08-28 |
| IT1033260B (it) | 1979-07-10 |
| US4098761A (en) | 1978-07-04 |
| NL7502422A (nl) | 1975-09-08 |
| DE2508097A1 (de) | 1975-09-11 |
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