CA2006134A1 - Thermally stable and light stable flame retardant thermoplastic polyolefin and polystyrene compositions - Google Patents
Thermally stable and light stable flame retardant thermoplastic polyolefin and polystyrene compositionsInfo
- Publication number
- CA2006134A1 CA2006134A1 CA002006134A CA2006134A CA2006134A1 CA 2006134 A1 CA2006134 A1 CA 2006134A1 CA 002006134 A CA002006134 A CA 002006134A CA 2006134 A CA2006134 A CA 2006134A CA 2006134 A1 CA2006134 A1 CA 2006134A1
- Authority
- CA
- Canada
- Prior art keywords
- flame retardant
- composition
- bis
- halogen
- polystyrene
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 81
- 239000003063 flame retardant Substances 0.000 title claims abstract description 70
- 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 abstract description 63
- 239000004793 Polystyrene Substances 0.000 title claims abstract description 25
- 229920002223 polystyrene Polymers 0.000 title claims abstract description 22
- 229920002397 thermoplastic olefin Polymers 0.000 title description 4
- -1 bicyclic phosphate compound Chemical class 0.000 claims abstract description 62
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- 239000010452 phosphate Substances 0.000 claims abstract description 18
- 229920005990 polystyrene resin Polymers 0.000 claims abstract description 11
- 229920005672 polyolefin resin Polymers 0.000 claims abstract description 7
- 229920001155 polypropylene Polymers 0.000 claims description 28
- 239000004743 Polypropylene Substances 0.000 claims description 26
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 claims description 23
- 239000000654 additive Substances 0.000 claims description 23
- 230000000996 additive effect Effects 0.000 claims description 14
- 229920001169 thermoplastic Polymers 0.000 claims description 14
- 239000004416 thermosoftening plastic Substances 0.000 claims description 14
- 229920005989 resin Polymers 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 239000011342 resin composition Substances 0.000 claims description 9
- 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 claims description 8
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- YBAIRXAJHLSFLB-UHFFFAOYSA-N BrC1(CCC(CC1)CC(Br)Br)Br Chemical compound BrC1(CCC(CC1)CC(Br)Br)Br YBAIRXAJHLSFLB-UHFFFAOYSA-N 0.000 claims description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 5
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 claims description 5
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 5
- 239000004611 light stabiliser Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 claims description 4
- 230000003078 antioxidant effect Effects 0.000 claims description 4
- 229920001577 copolymer Polymers 0.000 claims description 4
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 claims description 4
- UZOSVZSBPTTWIG-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-chlorocyclohexane Chemical compound ClC1C(Br)C(Br)C(Br)C(Br)C1Br UZOSVZSBPTTWIG-UHFFFAOYSA-N 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 238000005698 Diels-Alder reaction Methods 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 229920001748 polybutylene Polymers 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 239000002516 radical scavenger Substances 0.000 claims description 3
- LXIZRZRTWSDLKK-UHFFFAOYSA-N 1,3-dibromo-5-[2-[3,5-dibromo-4-(2,3-dibromopropoxy)phenyl]propan-2-yl]-2-(2,3-dibromopropoxy)benzene Chemical compound C=1C(Br)=C(OCC(Br)CBr)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(OCC(Br)CBr)C(Br)=C1 LXIZRZRTWSDLKK-UHFFFAOYSA-N 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- DHQKZHREWWXKQF-UHFFFAOYSA-I magnesium dicarbonoperoxoyloxyalumanyl hydroxy carbonate hydroxy carbonate Chemical group [Mg++].[Al+3].OOC([O-])=O.OOC([O-])=O.OOC([O-])=O.OOC([O-])=O.OOC([O-])=O DHQKZHREWWXKQF-UHFFFAOYSA-I 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 229920000098 polyolefin Polymers 0.000 abstract description 7
- 230000008859 change Effects 0.000 abstract description 5
- 238000010094 polymer processing Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 39
- 230000000052 comparative effect Effects 0.000 description 24
- 235000021317 phosphate Nutrition 0.000 description 20
- 230000015556 catabolic process Effects 0.000 description 12
- 238000006731 degradation reaction Methods 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 239000003381 stabilizer Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 125000002619 bicyclic group Chemical group 0.000 description 6
- 238000012545 processing Methods 0.000 description 5
- 229920005992 thermoplastic resin Polymers 0.000 description 5
- WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 230000002708 enhancing effect Effects 0.000 description 3
- 229920001519 homopolymer Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- XQKQZOLAVMIQHZ-UHFFFAOYSA-N 1,1-dibromo-3-(3,3-dibromopropoxy)propane Chemical compound BrC(Br)CCOCCC(Br)Br XQKQZOLAVMIQHZ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 229910052724 xenon Inorganic materials 0.000 description 2
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 2
- FWKIOSWFVPOWSM-UHFFFAOYSA-N 1,1,12,12,12-pentabromododecylbenzene Chemical compound BrC(Br)(Br)CCCCCCCCCCC(Br)(Br)C1=CC=CC=C1 FWKIOSWFVPOWSM-UHFFFAOYSA-N 0.000 description 1
- AUTSLLHNWAZVLE-UHFFFAOYSA-N 1,1,2,2,3-pentabromo-3-chlorocyclohexane Chemical compound ClC1(Br)CCCC(Br)(Br)C1(Br)Br AUTSLLHNWAZVLE-UHFFFAOYSA-N 0.000 description 1
- FIAXCDIQXHJNIX-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-ethylbenzene Chemical compound CCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br FIAXCDIQXHJNIX-UHFFFAOYSA-N 0.000 description 1
- ACRQLFSHISNWRY-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-phenoxybenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=CC=CC=C1 ACRQLFSHISNWRY-UHFFFAOYSA-N 0.000 description 1
- YATIGPZCMOYEGE-UHFFFAOYSA-N 1,3,5-tribromo-2-[2-(2,4,6-tribromophenoxy)ethoxy]benzene Chemical compound BrC1=CC(Br)=CC(Br)=C1OCCOC1=C(Br)C=C(Br)C=C1Br YATIGPZCMOYEGE-UHFFFAOYSA-N 0.000 description 1
- MVSVFZKDCHTUGD-UHFFFAOYSA-N 3,4-dibromobicyclo[2.2.1]heptane Chemical compound C1CC2(Br)C(Br)CC1C2 MVSVFZKDCHTUGD-UHFFFAOYSA-N 0.000 description 1
- NEUHYMIDXNTABG-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[1-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1C(C)N1C(=O)C(C(Br)=C(Br)C(Br)=C2Br)=C2C1=O NEUHYMIDXNTABG-UHFFFAOYSA-N 0.000 description 1
- ZYUVGYBAPZYKSA-UHFFFAOYSA-N 5-(3-hydroxybutan-2-yl)-4-methylbenzene-1,3-diol Chemical compound CC(O)C(C)C1=CC(O)=CC(O)=C1C ZYUVGYBAPZYKSA-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 101100481176 Bacillus subtilis (strain 168) thiE gene Proteins 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- PKTNMTDLDLSRDE-UHFFFAOYSA-N C1OC2(P(=O)=O)OCC1(CO)CO2 Chemical compound C1OC2(P(=O)=O)OCC1(CO)CO2 PKTNMTDLDLSRDE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 101100494344 Desulfobacterium autotrophicum (strain ATCC 43914 / DSM 3382 / HRM2) bzaF gene Proteins 0.000 description 1
- 101100001675 Emericella variicolor andJ gene Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical group 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- GHPGOEFPKIHBNM-UHFFFAOYSA-N antimony(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Sb+3].[Sb+3] GHPGOEFPKIHBNM-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 1
- NHADDZMCASKINP-HTRCEHHLSA-N decarboxydihydrocitrinin Natural products C1=C(O)C(C)=C2[C@H](C)[C@@H](C)OCC2=C1O NHADDZMCASKINP-HTRCEHHLSA-N 0.000 description 1
- UGQQAJOWXNCOPY-UHFFFAOYSA-N dechlorane plus Chemical compound C12CCC3C(C4(Cl)Cl)(Cl)C(Cl)=C(Cl)C4(Cl)C3CCC2C2(Cl)C(Cl)=C(Cl)C1(Cl)C2(Cl)Cl UGQQAJOWXNCOPY-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- MPRVXUYAJZZBHG-UHFFFAOYSA-K dicarbonoperoxoyloxyalumanyl hydroxy carbonate Chemical compound [Al+3].OOC([O-])=O.OOC([O-])=O.OOC([O-])=O MPRVXUYAJZZBHG-UHFFFAOYSA-K 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 1
- 238000010943 off-gassing Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000843 phenylene group Polymers C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000013502 plastic waste Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006216 polyvinyl aromatic Polymers 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003440 styrenes Polymers 0.000 description 1
- 125000003011 styrenyl group Polymers [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 101150029215 thiC gene Proteins 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07F9/65748—Esters of oxyacids of phosphorus the cyclic phosphorus atom belonging to more than one ring system
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
-
- 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
- C08K5/527—Cyclic esters
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/289,973 | 1988-12-20 | ||
| US28997388A | 1988-12-22 | 1988-12-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2006134A1 true CA2006134A1 (en) | 1990-06-20 |
Family
ID=23113986
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002006134A Abandoned CA2006134A1 (en) | 1988-12-20 | 1989-12-20 | Thermally stable and light stable flame retardant thermoplastic polyolefin and polystyrene compositions |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0401366A4 (ko) |
| JP (1) | JPH03502820A (ko) |
| KR (1) | KR910700007A (ko) |
| CA (1) | CA2006134A1 (ko) |
| WO (1) | WO1990006691A1 (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05500983A (ja) * | 1989-09-15 | 1993-02-25 | グレート・レークス・ケミカル・コーポレーション | 煤煙抑制難燃性熱可塑性樹脂組成物 |
| US5627915A (en) * | 1995-01-31 | 1997-05-06 | Princeton Video Image, Inc. | Pattern recognition system employing unlike templates to detect objects having distinctive features in a video field |
| AU711729B2 (en) | 1995-08-29 | 1999-10-21 | Exxon Chemical Patents Inc. | Radiation tolerant polypropylene and its useful articles |
| US6472456B1 (en) | 1997-06-30 | 2002-10-29 | Ciba Specialty Chemicals Corp. | Flame retardant compositions |
| US6599963B2 (en) | 1997-06-30 | 2003-07-29 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| JP2005519161A (ja) * | 2002-03-01 | 2005-06-30 | ダウ グローバル テクノロジーズ インコーポレイティド | 熱老化が改良された寸法安定性プロピレンポリマー発泡体 |
| MY139230A (en) * | 2002-10-17 | 2009-08-28 | Ciba Holding Inc | Flame retardant polymeric electrical parts |
| US7109260B2 (en) * | 2002-10-17 | 2006-09-19 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| JP4937610B2 (ja) * | 2005-04-12 | 2012-05-23 | 第一工業製薬株式会社 | 難燃性発泡ポリスチレン系樹脂およびその成形体 |
| CN102369243B (zh) * | 2009-03-19 | 2014-11-05 | 界面解决方案Ip有限责任公司 | 生物基聚合物组合物 |
| US20190256780A1 (en) * | 2016-07-29 | 2019-08-22 | Adeka Corporation | Flame-retardant composition and flame-retardant synthetic-resin composition |
| EP4431561A1 (de) | 2023-03-15 | 2024-09-18 | LANXESS Deutschland GmbH | Phosphorsäureester-zusammensetzungen für flammwidriges weich-pvc mit hoher thermostabilität |
| EP4431560A1 (de) | 2023-03-15 | 2024-09-18 | LANXESS Deutschland GmbH | Phosphorsäureester-zusammensetzungen für flammwidriges weich-pvc mit hoher farbstabilität |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3293327A (en) * | 1958-07-21 | 1966-12-20 | Hooker Chemical Corp | Cyclic phosphites and phosphates |
| NL154241C (ko) * | 1971-01-29 | 1900-01-01 | ||
| US4016139A (en) * | 1973-02-08 | 1977-04-05 | Michigan Chemical Corporation | Plastic composition comprising acrylonitrile-butadiene-styrene polymer, a bis-phenoxy flame retardant and a flame retardant enhancing agent |
| DE2621323A1 (de) * | 1976-05-13 | 1977-12-01 | Hoechst Ag | Neue, organische phosphite, verfahren zu ihrer herstellung und ihre verwendung als stabilisatoren |
| GB2075989B (en) * | 1980-05-13 | 1984-04-26 | Kyowa Chem Ind Co Ltd | Stabilized thermoplastic resin compositions |
| JPS59138260A (ja) * | 1983-01-28 | 1984-08-08 | Mitsubishi Petrochem Co Ltd | ポリフエニレンエ−テル樹脂組成物 |
| JPH07788B2 (ja) * | 1984-10-30 | 1995-01-11 | 丸菱油化工業株式会社 | 難燃剤組成物 |
-
1989
- 1989-12-15 WO PCT/US1989/005627 patent/WO1990006691A1/en not_active Application Discontinuation
- 1989-12-15 JP JP90502089A patent/JPH03502820A/ja active Pending
- 1989-12-15 EP EP19900901968 patent/EP0401366A4/en not_active Withdrawn
- 1989-12-15 KR KR1019900701817A patent/KR910700007A/ko not_active Application Discontinuation
- 1989-12-20 CA CA002006134A patent/CA2006134A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0401366A1 (en) | 1990-12-12 |
| KR910700007A (ko) | 1991-03-13 |
| WO1990006691A1 (en) | 1990-06-28 |
| JPH03502820A (ja) | 1991-06-27 |
| EP0401366A4 (en) | 1991-06-05 |
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