IL95673A - Smoke suppressed thermoplastic resin composition and a method for suppressing the tendency of thermoplastic resin compositions to smoke under conditions of burning - Google Patents
Smoke suppressed thermoplastic resin composition and a method for suppressing the tendency of thermoplastic resin compositions to smoke under conditions of burningInfo
- Publication number
- IL95673A IL95673A IL9567390A IL9567390A IL95673A IL 95673 A IL95673 A IL 95673A IL 9567390 A IL9567390 A IL 9567390A IL 9567390 A IL9567390 A IL 9567390A IL 95673 A IL95673 A IL 95673A
- Authority
- IL
- Israel
- Prior art keywords
- composition
- flame retardant
- smoke
- retardant agent
- chain
- Prior art date
Links
- 239000000779 smoke Substances 0.000 title claims description 38
- 239000011342 resin composition Substances 0.000 title claims description 16
- 229920005992 thermoplastic resin Polymers 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 claims description 61
- -1 bicyclic phosphate compound Chemical class 0.000 claims description 35
- 229910019142 PO4 Inorganic materials 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000012757 flame retardant agent Substances 0.000 claims description 25
- 239000010452 phosphate Substances 0.000 claims description 23
- 239000004800 polyvinyl chloride Substances 0.000 claims description 15
- 229920000915 polyvinyl chloride Polymers 0.000 claims description 15
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 239000004793 Polystyrene Substances 0.000 claims description 7
- 229920001291 polyvinyl halide Polymers 0.000 claims description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000347 magnesium hydroxide Substances 0.000 claims description 6
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 6
- 229920005672 polyolefin resin Polymers 0.000 claims description 6
- 229920002223 polystyrene Polymers 0.000 claims description 6
- 229920005990 polystyrene resin Polymers 0.000 claims description 6
- 150000004684 trihydrates Chemical class 0.000 claims description 6
- UUEDINPOVKWVAZ-UHFFFAOYSA-N bis(2-ethylhexyl) 3,4,5,6-tetrabromobenzene-1,2-dicarboxylate Chemical compound CCCCC(CC)COC(=O)C1=C(Br)C(Br)=C(Br)C(Br)=C1C(=O)OCC(CC)CCCC UUEDINPOVKWVAZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000004677 hydrates Chemical class 0.000 claims description 5
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 4
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 150000001642 boronic acid derivatives Chemical class 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 229920001577 copolymer Polymers 0.000 claims description 2
- 229920001748 polybutylene Polymers 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical class C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 2
- PKTNMTDLDLSRDE-UHFFFAOYSA-N C1OC2(P(=O)=O)OCC1(CO)CO2 Chemical compound C1OC2(P(=O)=O)OCC1(CO)CO2 PKTNMTDLDLSRDE-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 150000003868 ammonium compounds Chemical class 0.000 claims 2
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims 2
- 150000001463 antimony compounds Chemical class 0.000 claims 2
- 235000013877 carbamide Nutrition 0.000 claims 2
- 150000002357 guanidines Chemical class 0.000 claims 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 150000003672 ureas Chemical class 0.000 claims 2
- 239000003063 flame retardant Substances 0.000 description 33
- 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 description 30
- 235000021317 phosphate Nutrition 0.000 description 25
- 239000000654 additive Substances 0.000 description 16
- 229920001169 thermoplastic Polymers 0.000 description 11
- 239000004416 thermosoftening plastic Substances 0.000 description 11
- 230000000996 additive effect Effects 0.000 description 8
- 239000004014 plasticizer Substances 0.000 description 6
- UNYOJUYSNFGNDV-UHFFFAOYSA-M magnesium monohydroxide Chemical compound [Mg]O UNYOJUYSNFGNDV-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229920000098 polyolefin Polymers 0.000 description 4
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- JJXNVYMIYBNZQX-UHFFFAOYSA-N diphenyl (2-propan-2-ylphenyl) phosphate Chemical compound CC(C)C1=CC=CC=C1OP(=O)(OC=1C=CC=CC=1)OC1=CC=CC=C1 JJXNVYMIYBNZQX-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- RYUJRXVZSJCHDZ-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(OCCCCCCCC(C)C)OC1=CC=CC=C1 RYUJRXVZSJCHDZ-UHFFFAOYSA-N 0.000 description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 229910018316 SbOx Inorganic materials 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 239000003963 antioxidant agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012760 heat stabilizer Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 239000004611 light stabiliser Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 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
- YHMOQCYOOUHZSF-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[1-(2,3,4,5,6-pentabromophenoxy)ethoxy]benzene Chemical compound BrC=1C(Br)=C(Br)C(Br)=C(Br)C=1OC(C)OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br YHMOQCYOOUHZSF-UHFFFAOYSA-N 0.000 description 1
- 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 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
- ORYGKUIDIMIRNN-UHFFFAOYSA-N 1,2,3,4-tetrabromo-5-(2,3,4,5-tetrabromophenoxy)benzene Chemical compound BrC1=C(Br)C(Br)=CC(OC=2C(=C(Br)C(Br)=C(Br)C=2)Br)=C1Br ORYGKUIDIMIRNN-UHFFFAOYSA-N 0.000 description 1
- NQKVVCRUKCIGHX-UHFFFAOYSA-N 1,2,3-tribromo-4-[1-[2-(9,9-dibromononyl)phenoxy]ethoxy]benzene Chemical compound C=1C=C(Br)C(Br)=C(Br)C=1OC(C)OC1=CC=CC=C1CCCCCCCCC(Br)Br NQKVVCRUKCIGHX-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 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
- 239000004114 Ammonium polyphosphate Substances 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
- YBAIRXAJHLSFLB-UHFFFAOYSA-N BrC1(CCC(CC1)CC(Br)Br)Br Chemical compound BrC1(CCC(CC1)CC(Br)Br)Br YBAIRXAJHLSFLB-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-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
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 description 1
- QRSFFHRCBYCWBS-UHFFFAOYSA-N [O].[O] Chemical compound [O].[O] QRSFFHRCBYCWBS-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 235000019826 ammonium polyphosphate Nutrition 0.000 description 1
- 229920001276 ammonium polyphosphate Polymers 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910000410 antimony oxide Inorganic materials 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 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
- 239000003925 fat Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000002896 organic halogen compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- LPLPPIFARDQDDL-UHFFFAOYSA-N phenyl (2-propan-2-ylphenyl) hydrogen phosphate Chemical compound CC(C)C1=CC=CC=C1OP(O)(=O)OC1=CC=CC=C1 LPLPPIFARDQDDL-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 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
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920006216 polyvinyl aromatic Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- C08K5/527—Cyclic esters
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)
Description
A SMOKE SUPPRESSED THERMOPLASTIC RESIN COMPOSITION AND A METHOD FOR SUPPRESSING THE TENDENCY OF THERMOPLASTIC RESIN COMPOSITIONS TO SMOKE UNDER CONDITIONS OF BURNING BACKGROUND OF THE INVENTION Field of the Invention. This invention relates to flame retardant thermoplastic resin compositions that exhibit a reduced tendency to generate smoke under burning conditions. More particularly, this invention relates to thermoplastic compositions such as polyvinyl chloride ("PVC"), polystyrene and polyolefins, comprising bicyclic phosphate compound(s); and flame retardant agent(s). The compositions produced in accordance with this invention exhibit a reduced tendency to smoke under burning conditions .
Description of the Prior Art. It is known in the art that the flammability of thermoplastics, such as polystyrene, polyolefins, and polyvinyl halides, can be reduced by incorporation of a flame retardant agent. Typical flame retardant agents include reactive or additive halogenated organic compounds, inorganic fillers, and special formulations based on phosphorous and ammonium salts.
Although efficient in suppressing the rate of combustion in a resin system, most flame retardants tend to affect adversely one or more key properties of the resin. For example, many flame retardant additives are ineffective at producing low smoke ("smoke suppressed") formulations.
Recent public awareness about risk and hazard assessment during fire situations, and technical limitations of conventional flame retardant additives warrant a need for improved flame retardant thermoplastic compositions. In particular, a need exists for a thermoplastic composition that passes flammability standards with low smoke and combustion by-product formation, and does not detract from overall polymer performance.
Many prior art references describe the use of a variety of smoke additives in polystyrene and polyolefins. Modern Plastics Encyclopedia , Vol. 63, No. 10A, McGraw-Hill, Inc., pp. 179-180 (1986). However, the selection of a suitable smoke suppressant for thermoplastic resins is not predictable. Selection is particularly difficult when flame retardants are employed, exacerbated by the complex interaction between the polymer and the flame retardant agent.
Hechenbleikner , et al. describe in U.S. Patent No. 3,293,327 the production of bicyclic phosphites, phosphonates , thiophosphates , and selenophdsphates . These compositions are said to be stabilizers for vinyl halide resins. They are alleged to be useful as heat stabilizers for vinyl chloride resin, and as antioxidants for fats and oils. The Hechenbleikner patent does not specify the use of bicyclic phosphates to achieve low smoke thermoplastic resin compositions, nor does it disclose that cyclic phosphates of the present invention could be used with flame retardant agents to produce smoke suppressed flame retardant thermoplastic compositions.
British Patent No. 999,793 describes a process for producing organic phosphates by subjecting organic phosphites to reaction with peracetic acid. This patent shows a method for producing the most preferred bicyclic phosphate of the present invention, 2,6, 7-trioxa-l-phosphobicyclo[ 2.2.2] -octane-4- methanol-1-oxide and teaches the use of acetal ring-containing phosphates as plasticizers or functional fluids. The British patent, however, does not disclose the present invention. It does not mention bicyclic phosphates as being useful for flame retardant thermoplastic resins, nor that the most preferred bicyclic phosphate of the present invention can be used with flame retardant additives to yield improved smoke suppressed thermoplastic compositions.
Hills, et al. describe in U.S. Patent No. 3,873,496 a flame retardant polyester composition which contains 5 to 25 percent of a hydroxymethyl bicyclic phosphate compound as a flame retardant additive. Hills did not observe the ability for bicyclic phosphates to act as smoke suppressors for thermoplastic resin compositions which employ halogenated compounds as the primary flame retardant additive.
Halpern, et al. describe in U.S. Patent No. 4,341,694 a composition comprising 2 , 6 , 7-trioxa-l-phosphobicyclo[ 2.2.2 ] -octane-4-methanol-l-oxide and a nitrogen-containing co-additive, which are intumescent and are adaptable to flame retard polyolefins, polyvinylaromatic resins, polycarbonates, PVC and blends thereof. Halpern did not observe any smoke suppression of the present invention.
Parr, et al. describe in U.S. Patent No. 4,801,625 a flame resistant composition having (1) an organic polymeric substance in intimate contact with (2) a bicyclic phosphorous compound, and (3) a gas producing compound. Parr is silent on the use of bicyclic compounds to attain smoke suppressed flame retardation thermoplastic compositions.
Accordingly, a primary object of this invention is to provide smoke suppressed flame retardant thermoplastic compositions.
A related object is to provide flame retardant thermoplastic polyvinyl chloride compositions with a reduced tendency to smoke under burning conditions.
A further object is to provide polyvinyl chloride resin compositions incorporating bicyclic phosphate compound and flame retardants. - 6 - 95673/2 The foregoing and other objects, advantages and features of the present invention may be achievable with smoke suppressed thermoplastic polyvinyl halide, polyolefin or polystyrene resin compositions incorporating an effective amount of an additive mixture comprising a" flame retardant agent and a bicyclic phosphate compound.
More particularly, the invention provides a smoke suppressed thermoplastic resin composition comprising a polyvinyl halide, polyolefin or polystyrene resin; and an effective amount of a mixture comprising a smoke suppressant comprising at least one bicyclic phosphate compound of the formula: where X is OH, OR' , or OC(0)R' ; R is H or a saturated or unsaturated straight-chain or branched-chain C3.-C3.-7 alkyl; and R' is a saturated or unsaturated straight-chain or branched-chain C3.-C3.-7 alkyl; and a flame retardant agent as herein defined, differing in composition from said smoke suppressant, and being nitrogen-free.
Compoositions in accordance with the present invention exhibit a reduced tendency to smoke under burning conditions.
The invention also provides a method for suppressing the tendency of polyvinyl halide, polyolefin or polystyrene resins to smoke under conditions of burning, comprising the step of incorporating therein an effective amount of a - 6A - 95673/ 1 mixture comprising a smoke suppressant comprising at least one bicyclic phosphate compound of the formula: where X is OH, OR' , or OC(0)R' ; R is H or a saturated or unsaturated straight-chain or branched-chain -C^-, alkyl; R' is a saturated or unsaturated straight-chain or branched-chain C -C 7 alkyl; and a flame retardant agent as herein defined, differing in composition from said smoke suppressant, and being nitrogen-free.
Preferred bicyclic phosphates in accordance with this invention are compounds of Formula (I) where X is OH or OC(0)R' . The most preferred bicyclic compounds are 2 , 6 , 7-trioxa-phosphobicyclo[ 2.2.2 ] -octane-4-methanol-l-oxide (Compound BCP, that is, Formula [I] when R is H and X is OH), and 2,6, 7-trioxa-l-phosphobicyclo[ 2.2.2] -octane- -methanol , acetate, 1-oxide (Compound BCP-A, that is, when R is H and X is OC(0)CH3) The flame retardant agent employed in accordance with the present invention may be any common flame retardant agent which can be used to reduce the flammability of thermoplastic resins, such as halogenated compounds containing bromine and/or chlorine or inorganic materials, such as metal hydrates, metal borates, antimony-containing compounds, or phosphorous-containing compounds .
Preferred halogen-containing compounds are di- ( 2-ethylhexyl )tetrabromophthalate , hexabromocyclododecane , tetrabromobisphenol A, tetrabromobisphenol A bis- (dibromopropylether ) , dibromo(dibromoethyl)cyclohexane, tetrabromocyclooctane , bis- (dibromonorbornane dicarboximido ) ethane , bi s- ( tetrabromophthalimido ) ethane , Diels-Alder adduct of chlorinated cyclopentadiene and an unsaturated cycloaliphatic compound, bis- ( tribromophenoxyethyl ) -tetrabromobisphenol A ether, pentabromodiphenyl ether, octabromodiphenyl ether, decabromodiphenyl ether, bis- (tribromophenoxy) ethane, bis- (pent bromophenoxy) ethane , chloropentabromocyclohexane , ( tribromophenoxy) - (dibromononylphenoxy) ethane , pentabromoethylbenzene , pentabromododecylbenzene , carbonate oligomers of tetrabromob sphenol A, poly (bromostyrene ) , and brominated polystyrene, poly (bromophenylene ) ether, and mixtures thereof. Particularly preferred is di-(2-ethylhexyl)tetrabromophthalate.
Substantially any suitable metal hydrates and oxides may be employed as flame retardant agents, including hydrates and oxides of aluminum, iron, zinc, magnesium, tin, molybdenum and antimony. Alumina trihydrate, magnesium hydroxide, and antimony trioxide are the preferred compounds in this class.
Suitable metal boron-containing flame retardant compounds include zinc, barium, calcium, magnesium, cadmium and mercury. Zinc borate is the preferred compound in this class.
Substantially any suitable phosphorus-containing compound may be used as a flame retardant agent, including ammonium polyphosphate, arylphosphates , alkarylphosphates and alkylphosphates . Particularly preferred are phenyl isopropylphenyl phosphate and isodecyldiphenyl phosphate commercially available from FMC Corporation under the trademarks Kronitex 100 and Santicizer 148.
The foregoing flame retardant compounds are added to thermoplastic resins at effective levels such that the resultant resin composition may be rendered flame retardant.
Thermoplastic resins which may be treated in accordance with the invention include thermoplastics such as polyvinyl halides, polystyrene, and homopolymers and copolymers of polypropylene, polyethylene, and polybutylene . Polyvinyl chloride is most preferred in accordance with this invention.
The scope of the present invention also includes the incorporation of other additives in the composition so far as to produce a particular end result. Such additives include, without blowing agents, heat stabilizers, light stabilizers, plasticizers , pigments, preservatives, ultraviolet light stabilizers, fillers, antioxidants, antistatic agents and other materials well known to those skilled in the art, for example, as described in Modern Plastics Encyclopedia, Vol. 63_, No. 10A, McGraw-Hill, Inc. (1986).
The bicyclic phosphates of the present invention may be used alone or as mixtures of any such compounds. When mixtures of bicyclic phosphates are employed, substantially any combinations of amounts and proportions of the individual compounds may be used. The use of Compound BCP and Compound BCP-A is especially preferred in accordance with this invention.
The bicyclic phosphate may be employed at substantially any level because even very low levels are believed to assist in smoke suppression. Preferably it is present at a level of at least 2 percent and preferably about 3 percent up to about 20 percent by weight of the composition.
The flame retardant agents of the present invention may be used alone or as mixtures of any such compounds. When mixtures of flame agents are employed, substantially any combinations of amounts and proportions of the individual compounds may be used. The use of di- ( 2-ethylhexyl ) - tetrabromophthalate, alumina trihydrate, magnesium hydroxide, zinc borate, antimony trioxide, and alkylaryl phosphates are especially preferred in accordance with this invention.
Desirably, flame retardants are employed at a level of about 2 to 50 percent by weight of the composition, preferably about 3 to 20 percent, depending on the specific flame retardant and thermoplastic resin employed. Operative and preferred ranges for various flame retardants in accordance with this invention are given in the Table I .
TABLE I OPERATING RANGES MATERIAL OPERATIVE RANGE PREFERRED RANGE BrFr 2-50 3-20 AAP 2-50 3-20 ATH 2-50 5-20 MgOH 2-50 5-10 ZnBor 2-50 5-10 SbOx 1-15 5-10 BrFr - di- ( 2-ethylhexyl ) tetrabromophthalides brominated flame retardant AAP - alkylarylphosphate (Kronitex 100 - FMC Corp. ) ATH - alumina trihydrate MgOH - magnesium hydroxide ZnBor - zinc borate SbOx - antimony oxide Desirably, the bicyclic phosphate compound and flame retardant are provided as a mixture useful as an additive which may be added to polystyrene or polyolefin resin compositions. The additive mixture utilizes bicyclic phosphate and flame retardant in a weight ratio lying in the range of about 1:25 to 20:1, most preferably, about 3:20 to 20:3.
The additive mixture is incorporated into the polymer composition at an effective level such that the resulting resin composition is rendered flame retardant. In general, the additive mixture is provided in the flame retardant at a level of about 2 - 50 percent by weight of the resin composition, preferably about 3 - 30 percent by weight.
Practice of the present invention is illustrated by the following examples, which are given to illustrate the invention and should not be construed as limiting its scope.
EXAMPLES Preparation of Polyvinylchloride Resin Systems. A general purpose polyvinylchloride ("PVC") resin was used in the study. PVC resin, powdered additives and flame retardant were blended in a mixing bowl and warmed to 90°C. Liquid plasticizer was added, and the admixture was compounded on a two-roll mill at 160°C. The compounded PVC material was compression molded at 180°C.
Table II shows examples of the use of Compound BCP in flexible PVC formulations. The general formulation used is as follows: Material ¾ by weight PVC Resin varied Compound BCP varied (see Table) Flame Retardant varied (see Table) Dioctylphthalate Plasticizer varied (see below) Epoxidized Soya Plasticizer 5 Stabilizer 3 The amount of dioctyl phthalate ("DOP") plasticizer was adjusted to give compositions with comparable physical properties (i.e., approximately 90 Shore A hardness) and flammability (approximately 30 01) performance.
Flammability Test Procedures. The following flammabi lity tests were used throughout the study: Test Method Description ASTM D-2863 Limiting Measurement of the minimum oxygen Oxygen Index necessary to sustain burning of a vertically supported sample for three minutes. High values indicate improved resistance to burning.
NBS Smoke Chamber Smoke density determinations ASTM -662 under smoldering conditions. Low values indicate low smoke evolution.
A series of experimental and comparative studies were performed using the foregoing techniques. The data are given in Table II.
TABLE II FLAMMABILITY AND PHYSICAL PROPERTY PERFORMANCE FLEXIBLE POLY INYLCHLORIDE COMPOSITIONS EXAMPLE AMOUNT OF FLAME RETARDANT NBS SMOKE OXYGEN HARDNESS NUMBER BCP TYPE AMOUNT SMOLDERING INDEX SHORE A Wt % wt % ASTM -662 ASTM ASTM D-2863 CONTROL 5 .0 0.0 170 30 90 1 5 .0 BrFr 10.0 165 30 90 COMP 2 0 .0 BrFr 10.0 210 30 90 2 5 .0 AAP 15.0 160 30 90 COMP 3 0 .0 AAP 15.0 200 30 90 3 5 .0 ATH 15.0 145 30 90 COMP 4 0 .0 ATH 15.0 160 30 90 4 5 .0 MgOH 15.0 140 30 90 COMP 5 0 .0 MgOH 15.0 165 30 90 5 5 .0 ZnBor 15.0 130 30 90 COMP 6 0 .0 ZnBor 15.0 155 30 90 BCP - Preferred bicyclic phosphate BrFr - di- (2-ethylhexyl ) tetrabromophthalates AAP - alkylarylphosphate (Kronitex 100 - FMC Corp.) ATH - alumina trihydrate MgOH - magnesium hydroxide ZnBor - zinc borate These data demonstrate the patentability of the subject invention as follows. The Control Example shows the effect of 5.0% BCP alone on the smoke performance of a 30 01 flexible PVC composition. Comparative Examples 2-6 show the effect of various flame retardants on smoke performance when Compound BCP is not present.
Example 1 illustrates the invention when the flame retardant is a bromine-containing flame retardant. Example 2 illustrates the invention when the flame retardant is phosphate-containing flame retardant (an alkarylphosphate ) . Example 3-5 illustrate the invention when the flame retardant is an inorganic flame retardant.
In the case of each invention composition, compositions comprising a bicyclic phosphate (Compound BCP) and a flame retardant had lower smoke than the Control (i.e., a system without any additional flame retardant agent) or the corresponding Comparative Examples 2-6 (i.e., a system without bicyclic phosphate).
Claims (18)
1. A smoke suppressed thermoplastic resin composition, comprising: a polyvinyl halide, polyolefin or polystyrene resin; and an effective amount of a mixture comprising: a smoke suppressant comprising at least one bicyclic hos ha e compound of the formula: where X is OH, OR', or OC(0)R'; R is H or a saturated or unsaturated straight-chain or branched-chain C -C1V alkyl; and R 1 is a saturated or unsaturated straight-chain or branched-chain C;,.-C17 alkyl; and a flame retardant agent as hereinbefore defined, differing in composition from said smoke suppressant, and being nitrogen-free.
2. A composition as claimed in claim 1, wherein the flame retardant agent is a member selected from the group consisting of alogenated compounds, metal hydrates, metal borates, antimony compounds, phosphorous compounds, and mixtures thereof.
3. A composition as claimed in claim 1, wherein the flame retardant agent is a member selected from the group consisting of di- ( 2-ethylhexyl) tetrabromophthalate, alumina trihydrate, magnesium hydroxide, antimony trioxide, zinc borate and alkarylphosphates . - 17 - 95673/2
4. A composition as claimed in claim 1, wherein the bicyclic phosphate compound is 2,6,7-trioxa-phosphobicyclo[2.2.2]-octane-4 -methanol-1 -oxide; or 2,6,7-trioxa-l-phosphobicyclo[2.2.2]-octane-4-methanol, acetate, 1-oxide.
5. A composition as claimed in claim 1, wherein the resin is a member selected from the group consisting of polyvinyl chloride, polystyrene and polyethylene, polypropylene and polybutylene homo- and copolymers.
6. A composition, as claimed in claim 5, wherein the resin is polyvinyl chloride.
7. A composition as claimed in claim 1, wherein the weight ratio of bicyclic phosphate compound to flame retardant agent lies in the range of about 1:25 to 20:1.
8. A composition as claimed in claim 1, wherein the mixture of bicyclic phosphate compound and flame retardant agent is provided in the resin composition at a level lying in the range of about 2 to 50 percent by weight of the overall composition.
9. A method for suppressing the tendency of polyvinyl halide, polyolefin or polystyrene resins to smoke under conditions of burning, comprising the step of incorporating therein an effective amount of a mixture comprising: a smoke suppressant comprising at least one bicyclic phosphate compound of the formula: - 18 - 95673/3 where X is OH, OR' or OC(0)R' ; R is H or a saturated or unsaturated straight-chain or branched-chain CxrC17 alkyl, R' is a saturated or unsaturated straight-chain or branched-chain d-Ci, alkyl; and a flame retardant agent as hereinbefore defined, differing in composition from said smoke suppressant, and being nitrogen- free .
10. A method as claimed in claim 9, wherein the flame retardant agent is a member selected from the group consisting of halogenated compounds, metal hydrates, metal borates, antimony compounds, phosphorous compounds, and mixtures thereof.
11. A method as claimed in claim 9, wherein the flame retardant agent is a member selected from the group consisting of di-{2-ethylhexyl) tetrabromophthalate, alumina trihydrate, magnesium hydroxide, antimony trioxide, zinc borate and alkarylphosphates .
12. A method as claimed in claim 9, wherein the bicyclic phosphate compound is 2,6,7-trioxa-phosphobicyclo[2.2.2]-octane-4-methanol-1-oxide; or 2,6,7-trioxa-l-phosphobicyclo[2.2.2]-octane-4-methanol, acetate, 1-oxide.
13. A method as claimed in claim 9, wherein the weight ratio of bicyclic phosphate compound to flame retardant agent lies in the range of about 1:25 to 20:1. - 19 - 95673/2
14. The composition of claim 1, and which is substantially free of ammonium compounds, amines, ureas, guanidines, guanamines, s-triazines, amino acids, peptides and salts thereof.
15. The composition of claim 1, and which consists essentially of said resin, said flame retardant agent, and said at least one bicyclic phosphate compound.
16. The composition of claim 1, in which X is OH and in which R is H.
17. The composition of claim 9, and which is substantially free of ammonium compounds, amines, ureas, guanidines, guanamines, s-triazines, amino acids, peptides and salts thereof.
18. The method of claim 9, in which said mixture consists essentially of said flame retardant agent and said at least one bicyclic phosphate. for the Applicant: WOLFF, BREGMAN AND GOLLER
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40814289A | 1989-09-15 | 1989-09-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL95673A0 IL95673A0 (en) | 1991-06-30 |
| IL95673A true IL95673A (en) | 1995-05-26 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9567390A IL95673A (en) | 1989-09-15 | 1990-09-13 | Smoke suppressed thermoplastic resin composition and a method for suppressing the tendency of thermoplastic resin compositions to smoke under conditions of burning |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0500608A1 (en) |
| JP (1) | JPH05500983A (en) |
| KR (1) | KR927003711A (en) |
| AU (2) | AU6625390A (en) |
| CA (1) | CA2025172A1 (en) |
| IL (1) | IL95673A (en) |
| WO (1) | WO1991004294A1 (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997041173A1 (en) * | 1996-04-26 | 1997-11-06 | Akzo Nobel N.V. | Flame retardant composition for polymers |
| US10851228B2 (en) | 2018-07-26 | 2020-12-01 | FSIT Services LLC | Flame-retardant composition |
| CN110894331B (en) * | 2019-12-19 | 2022-04-08 | 天津金发新材料有限公司 | Environment-friendly low-smoke flame-retardant HIPS material and preparation method thereof |
| CN115340736B (en) * | 2022-05-20 | 2023-09-29 | 扬州实嘉电缆材料有限公司 | Nitrogen-phosphorus flame retardant modified polyvinyl chloride fireproof cable material |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4341694A (en) * | 1981-07-06 | 1982-07-27 | Borg-Warner Corporation | Intumescent flame retardant compositions |
| US4801625A (en) * | 1987-08-27 | 1989-01-31 | Akzo America Inc. | Bicyclic phosphate ether, ester, and carbonate intumescent flame retardant compositions |
| JPH03502820A (en) * | 1988-12-22 | 1991-06-27 | グレート・レークス・ケミカル・コーポレーション | Heat and light stable flame retardant thermoplastic polyolefin and polystyrene compositions |
-
1990
- 1990-09-12 CA CA002025172A patent/CA2025172A1/en not_active Abandoned
- 1990-09-12 KR KR1019920700594A patent/KR927003711A/en not_active Ceased
- 1990-09-12 WO PCT/US1990/005147 patent/WO1991004294A1/en not_active Ceased
- 1990-09-12 EP EP19900916156 patent/EP0500608A1/en not_active Withdrawn
- 1990-09-12 JP JP2514943A patent/JPH05500983A/en active Pending
- 1990-09-12 AU AU66253/90A patent/AU6625390A/en not_active Abandoned
- 1990-09-13 IL IL9567390A patent/IL95673A/en not_active IP Right Cessation
-
1994
- 1994-08-18 AU AU70355/94A patent/AU7035594A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2025172A1 (en) | 1991-03-16 |
| EP0500608A1 (en) | 1992-09-02 |
| AU6625390A (en) | 1991-04-18 |
| KR927003711A (en) | 1992-12-18 |
| WO1991004294A1 (en) | 1991-04-04 |
| IL95673A0 (en) | 1991-06-30 |
| AU7035594A (en) | 1994-11-03 |
| JPH05500983A (en) | 1993-02-25 |
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