WO1990000165A1 - Flame retardant higher alkyl bisphenoxy alkanes and their application to abs polymer systems - Google Patents
Flame retardant higher alkyl bisphenoxy alkanes and their application to abs polymer systems Download PDFInfo
- Publication number
- WO1990000165A1 WO1990000165A1 PCT/US1989/002796 US8902796W WO9000165A1 WO 1990000165 A1 WO1990000165 A1 WO 1990000165A1 US 8902796 W US8902796 W US 8902796W WO 9000165 A1 WO9000165 A1 WO 9000165A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- flame retardant
- halogenated
- higher alkyl
- ethane
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 53
- 239000003063 flame retardant Substances 0.000 title claims abstract description 41
- 150000001335 aliphatic alkanes Chemical class 0.000 title claims abstract description 39
- 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 34
- 229920000642 polymer Polymers 0.000 title description 10
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims abstract description 53
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 22
- 230000002708 enhancing effect Effects 0.000 claims abstract description 16
- 239000012757 flame retardant agent Substances 0.000 claims abstract description 15
- 239000000203 mixture Substances 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 34
- 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 24
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 claims description 24
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000460 chlorine Chemical group 0.000 claims description 9
- 229910052801 chlorine Chemical group 0.000 claims description 9
- 239000011342 resin composition Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 6
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical group O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 2
- 150000002484 inorganic compounds Chemical class 0.000 claims description 2
- 229910010272 inorganic material Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- YPFPSWOBTLQFMC-UHFFFAOYSA-N 1,2,3-tribromo-4-[2-[2-(12,12-dibromododecyl)phenoxy]ethoxy]benzene Chemical compound BrC(Br)CCCCCCCCCCCC1=CC=CC=C1OCCOC1=CC=C(Br)C(Br)=C1Br YPFPSWOBTLQFMC-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229940126062 Compound A Drugs 0.000 description 11
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 11
- 238000013019 agitation Methods 0.000 description 11
- 229920003023 plastic Polymers 0.000 description 11
- 239000004033 plastic Substances 0.000 description 11
- -1 tribromophenoxy-ethyl Chemical group 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 239000004597 plastic additive Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 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 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 6
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 5
- 0 OC1CC(C2*CCCC2)=CCC1 Chemical compound OC1CC(C2*CCCC2)=CCC1 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 229920001169 thermoplastic Polymers 0.000 description 5
- 239000004416 thermosoftening plastic Substances 0.000 description 5
- BSWWXRFVMJHFBN-UHFFFAOYSA-N 2,4,6-tribromophenol Chemical compound OC1=C(Br)C=C(Br)C=C1Br BSWWXRFVMJHFBN-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000006277 halobenzyl group Chemical group 0.000 description 4
- 125000005059 halophenyl group Chemical group 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 108010021119 Trichosanthin Proteins 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000000979 retarding effect Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- PAYCLGHFQKQABN-UHFFFAOYSA-N 2-(2,4,6-tribromophenoxy)ethyl benzenesulfonate Chemical compound BrC1=CC(Br)=CC(Br)=C1OCCOS(=O)(=O)C1=CC=CC=C1 PAYCLGHFQKQABN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 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
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 150000003839 salts Chemical class 0.000 description 2
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- NDRKXFLZSRHAJE-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2,3,4-tribromophenyl)benzene Chemical group BrC1=C(Br)C(Br)=CC=C1C1=C(Br)C(Br)=C(Br)C(Br)=C1Br NDRKXFLZSRHAJE-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
- IFCRAXQUCIIGJZ-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[2-[2-(9,9-dibromononyl)phenoxy]ethoxy]benzene Chemical compound BrC(Br)CCCCCCCCC1=CC=CC=C1OCCOC1=C(Br)C(Br)=C(Br)C(Br)=C1Br IFCRAXQUCIIGJZ-UHFFFAOYSA-N 0.000 description 1
- NZDXHOQDUNESKR-UHFFFAOYSA-N 1,2,3-tribromo-4-[1-(2,3,4-tribromophenoxy)decoxy]benzene Chemical compound C=1C=C(Br)C(Br)=C(Br)C=1OC(CCCCCCCCC)OC1=CC=C(Br)C(Br)=C1Br NZDXHOQDUNESKR-UHFFFAOYSA-N 0.000 description 1
- YVVYMSXDQGDASK-UHFFFAOYSA-N 1,2,3-tribromo-4-[2-(2,3,4-tribromophenoxy)ethoxy]benzene Chemical compound BrC1=C(Br)C(Br)=CC=C1OCCOC1=CC=C(Br)C(Br)=C1Br YVVYMSXDQGDASK-UHFFFAOYSA-N 0.000 description 1
- FCLGRFFRLJJTQV-UHFFFAOYSA-N 1,2,3-tribromo-4-[2-[2-(8,8-dibromooctyl)phenoxy]ethoxy]benzene Chemical compound BrC(Br)CCCCCCCC1=CC=CC=C1OCCOC1=CC=C(Br)C(Br)=C1Br FCLGRFFRLJJTQV-UHFFFAOYSA-N 0.000 description 1
- XTZXCZHXIXTXAY-UHFFFAOYSA-N 1,3,5-tribromo-2-(2-bromoethyl)-4-[2,4,6-tribromo-3-(2-bromoethyl)phenoxy]benzene Chemical compound BrCCC1=C(Br)C=C(Br)C(OC=2C(=C(CCBr)C(Br)=CC=2Br)Br)=C1Br XTZXCZHXIXTXAY-UHFFFAOYSA-N 0.000 description 1
- OXDVUOXPEVNHQO-UHFFFAOYSA-N 1-(2-bromoethyl)-3-[3-(2-bromoethyl)-2-(9,9-dibromononyl)phenoxy]-2-(9,9-dibromononyl)benzene Chemical compound BrCCC1=CC=CC(OC=2C(=C(CCBr)C=CC=2)CCCCCCCCC(Br)Br)=C1CCCCCCCCC(Br)Br OXDVUOXPEVNHQO-UHFFFAOYSA-N 0.000 description 1
- XGLVDUUYFKXKPL-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n,n-bis[2-(2-methoxyethoxy)ethyl]ethanamine Chemical compound COCCOCCN(CCOCCOC)CCOCCOC XGLVDUUYFKXKPL-UHFFFAOYSA-N 0.000 description 1
- FIPQPPTZIYUCKM-UHFFFAOYSA-N 2-(9,9-dibromononyl)phenol Chemical compound OC1=CC=CC=C1CCCCCCCCC(Br)Br FIPQPPTZIYUCKM-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 229910052797 bismuth Inorganic materials 0.000 description 1
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- 238000009835 boiling Methods 0.000 description 1
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- 229920001577 copolymer Polymers 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
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- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SSDSCDGVMJFTEQ-UHFFFAOYSA-N octadecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SSDSCDGVMJFTEQ-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- 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
Definitions
- the present invention relates to a plastic additive composition and more particularly to a plastic additive composition
- this invention relates to a nonblooming flame retardant ABS resin composition incorporating the halogenated unsymmetrical higher bisphenoxy alkanes.
- plastic additive compositions are an important class of industrial materials. Plastic additives are used to enhance or modify the properties of commercially available polymers. The use of plastic additives allows a relatively small number of commercially available polymers to be tailored to a myriad of uses. Those skilled in the art will know that the selection of an application of a specific plastic additive is unpredictable at best. Therefore, additive manufacturers must take a sophisticated approach and offer a range of products to achieve the desired result.
- Plastic additive compositions can be used as plasticizers, flame retardants, flow modifiers, or impact modifiers in resin systems, heat transfer fluids, or hydraulic fluids.
- One important use of plastic additive compositions is as flame retardant agents in resin systems.
- Most flame retardant agents although efficient in their function of retarding the rate of combustion in a resin system, have a tendency to affect adversely one or more key properties of the resin. For example, many flame retardant additives tend to reduce the impact strength of the resin; to migrate from the resin composition, resulting in a phenomena known as "bloom"; to
- ABS thermoplastics offer a good balance of
- ABS thermoplastics are used in. a wide variety of applications because of their properties and moderate costs.
- ABS thermoplastics are used by telephone equipment, electronic, and automotive manufacturers who require materials of high impact strength.
- retardant agents require that certain key properties be maintained.
- key properties include impact strength, light stability and retention of surface aesthetic properties.
- manufacturers of computer housings desire a thermoplastic ABS resin which is flame retardant, light stable, and resistant to bloom.
- compositions obtained using these various bromine containing compounds have a tendency to change color on exposure to light, to develop a reduction in surface gloss, and to form deposits of flame retardant agents on the polymer surface.
- compositions of the flame retardants are depicted by the following formula:
- A is a cyano, nitro, lower alkoxy, lower alkyl, fluorine, dialkylamino, phenyl,
- R is chosen from the following group:
- U.S. Patent No. 3,883,479 issued to Anderson, .et al. discloses plastic compositions containing ABS and symmetrical bisphenoxy compounds.
- the bisphenoxy compounds have the formula: wherein Z is bromine, m and m' are integers having a value of 1-4, i and i' are integers having a value of 1 or 2.
- the alkylene is a straight or branched chain alkylene group having from 1 to 6 carbon atoms.
- A is to be selected from the group consisting of cyano, nitro, lower alkoxy, lower alkyl (defined as CH 3 , C 2 H 5 , C 3 H 7 or C 4 H 9 ), fluorine, dialkylamino, phenyl,
- the flame retardants have the formula:
- A is chosen from the group consisting of cyano, nitro, lower alkoxy, lower alkyl, fluorine, diakylamino, phenyl, halo-phenyl, benzyl or halo-benzyl group.
- compositions of the flame retardants have the formula:
- Z is bromine or chlorine
- m and m' are integers having a value of 1 to 5
- i and i' are integers having a value of 0 to 2
- HBCA is a halo-branched alkylene group having from 1 to 6 carbon atoms
- A is cyano, nitro, lower alkoxy, lower alkyl (C 1 -C 4 ), fluorine, dialkylamino, phenyl, halo-phenyl, benzyl or
- n and m' are integers having a value between 1 and 5 and the alkylene is a straight or branched alkylene group containing 1 to 6 carbon atoms.
- Anderson, et al., U.S. Patent No. 4,016,139 disclose a composition containing an ABS polymer, a symmetrical bisphenoxy flame retardant and a flame retardant enhancing agent.
- the bisphenoxy flame retardant has the following formula: wherein Z is bromine, m and m' are integers having a value of 1 to 5 so that the total bromine atom content ranges from 6 to 10 atoms, and T is a straight chain or branched chain carbon group having 1 to 4 carbon atoms.
- composition contains an ABS polymer and a symmetrical bisphenoxy compound having the formula:
- alkylene is a straight or branched chain alkylene group having from 1 to 6 carbon atoms and A is chlorine.
- a primary object of this invention is to provide new unsymmetrical higher alkyl halogenated bisphenoxy alkanes.
- Another object of the invention is to provide halogenated unsymmetrical higher alkyl bisphenoxy alkanes having utility as flame retardant agents.
- Yet another object of the invention is to provide halogenated unsymmetrical higher alkyl bisphenoxy alkanes having utility as non-blooming flame
- An additional object of the present invention is to provide an agent capable of flame retarding ABS resin compositions without exhibiting problems of bloom, heat or light instability or any of the other disadvantages of the prior art ABS flame retardant agents.
- the bisphenoxy alkane used in accordance with this invention is a brominated unsymmetrical higher alkyl bisphenoxy ethane.
- the preferred bisphenoxy alkane used in accordance with this invention is a brominated unsymmetrical higher alkyl bisphenoxy ethane.
- brominated bisphenoxy ethane contains between 40 and 70 percent by weight of bromine.
- the invention contemplates incorporating an effective amount of halogenated unsymmetrical higher alkyl bisphenoxy alkane and an enhancing agent into a normally combustible ABS resin to obtain a flame retardant ABS resin composition.
- the compositions of this invention preferably comprise about 50 to 90 percent ABS thermoplastic resin, about 5 to 30 percent halogenated unsymmetrical higher alkyl bisphenoxy alkane and about 0.1 to 15 percent enhancing agent, all by weight of the composition.
- novel compositions of this invention are distinguished from the known bisphenoxy compositions by improved properties.
- compositions are stable to light and heat, have good flame retardant properties, and, most importantly, compositions incorporating the novel compounds do not bloom.
- compositions of matter are halogenated unsymmetrical higher alkyl bisphenoxy alkanes of the following formula:
- R 3 is a straight or branched alkylene group from methyl (CH 3 ) to dodecyl (C 12 H 25 ) such as cyclohexane for example; and if n is 1, R 1 is not R 2 .
- the novel composition of matter contains some minor amounts of symmetrical halogenated higher alkyl bisphenoxy alkanes. The minor amounts in the composition do not effect the utility of the composition as a non-blooming flame retardant agent.
- X is bromine
- the bromine content should be between approximately 40 percent and 70 percent by weight.
- Especially preferred bisphenoxy compounds are those compounds where x is 3, z is 2, and n is zero.
- X is bromine
- R 2 is either octyl (C 8 H 17 ) or nonyl (C 9 H 19 ) and R 3 is ethylene.
- the preferred novel plastic additive compositions, brominated bisphenoxy ethanes are prepared in a
- X and Y are independently bromine or chlorine.
- the preferred method of synthesis is to react the phenate salt containing the least alkyl content with a large excess of 1,2-dibromoethane (>4 moles/mole phenate) in a polar, high-boiling solvent such as propylene glycol. The excess dibromoethane is then preferably removed by distillation before reacting the intermediate with the second phenate salt.
- the compounds listed in Table 1 are examples of compounds synthesized by the preferred synthesis method. The list is not intended to be exhaustive or to limit the scope of the invention.
- the brominated alkyl phenols were produced from commercially available alkyl phenols using techniques known in the art.
- bisphenoxy ethane is used in a plastic formulation, it should be employed in amounts of 0.5 to 30 percent by weight of plastic formulation.
- the most preferred weight percent of brominated bisphenoxy ethane in the plastic formulation is 5 percent to 20 percent.
- This invention also encompasses use of
- bisphenoxy alkanes are useful in the preparation of non-blooming flame retardant ABS resins.
- novel compositions of this invention are distinguished from known flame retardant ABS compositions by improved properties.
- ABS Preferred novel flame retardant ABS
- compositions may be prepared by admixing from about 50% to about 90% by weight thermoplastic ABS resin; from about 5% to about 30% by weight halogented unsymmetrical higher alkyl bisphenoxy alkane compounds; from about 0.1% to about 15% by weight enhancing agent, where the percentages are based on the total weight of the resulting admixture of these three components.
- the compositions of this invention comprise about 60 to 90% ABS resin; about 10 to 30% halogenated unsymmetrical higher alkyl bisphenoxy alkane compound; and about 2 to 10% enhancing agent.
- the ABS resin may be any thermoplastic resin formed by blending a styrene/acrylonitrile copolymer with butadiene-based rubber, or by grafting
- substantially any suitable acrylonitri le-butadiene-styrene composition may be used, containing each component of the terpolymer in substantially any proportion.
- the ABS may contain or may be substantially free of other additives such as stabilizers , plasticizers , dyes , pigments , fillers and the like .
- the preferred plastic composition additives in the preparation of non-blooming flame retardant ABS resins are all unsymmetrical , that i s R 1 is not R 2 where n is 1 .
- the preferred additives in accordance with this invention include :
- ABS flame retardant compositions of this invention also desirably incorporate one or more
- accordance with this invention comprise the oxides and halides of groups IV-A and V-A of the periodic table; organic or inorganic compounds of
- Preferred enhancing agents in accordance with this invention are the oxides of antimony, arsenic and bismuth, with the oxides of antimony being
- Antimony trioxide is the most preferred enhancing agent used in the compositions of this invention. As noted, the enhancing agent is supplied at the level of about 0.1-15 percent by
- the enhancing agent is used at a level of about 2-10 percent by weight.
- additives include, without limitation, heat
- Step I 2,4,6-Tribromophenol (856 grams, 2.6 moles), phenol (6 grams), sodium carbonate (180 grams, 1.7 moles) and propylene glycol (1036 grams) are combined in a five-liter reactor equipped with a mechanical stirrer. The mixture is brought to 100oC with agitation and held for one hour.
- 1,2-Dibromoethane (1950 grams, 10.4 moles) is added to the reactor all at once. The temperature is returned to 100oC and held for an additional three hours with high agitation. Without allowing the reaction mixture to cool, agitation is discontinued, the phases are allowed to separate. Methanol (6 liters) is placed in a 12-liter reactor with
- Step I Dibromononylphenol (2270 grams, 6.0
- Step II 2,4,6-Tribromophenol (1985 grams, 6.0 moles), phenol (14 grams), sodium carbonate (382
- the mixture is held at 145oC with vigorous agitation for four hours. With the stirrer off, the reactor is cooled to 35oC and the upper phase decanted. The lower phase is dissolved in methylene chloride (2.5 liter). After washing with dilute hydrochloric acid, the solvent is
- Step I Dibromononylphenol (983 grams, 2.6 moles), sodium carbonate (180 grams, 1.7 moles), 1,2-dibromoethane (1950 grams, 10.4 moles),
- TDA-1 tris(2-(2-methoxyethoxy)ethyl) amine or TDA-1 (84 grams) are combined in a 3-liter reactor equipped with a mechanical stirrer and Dean-Stark trap. The mixture is heated to 130oC and held for four hours. After cooling, the mixture is filtered, and the excess dibromoethane is removed using a wiped film evaporator at 100oC and 20 torr vacuum.
- Step II The product from Step I which is predominantly 3-bromoethyl-dibromononylphenyl ether and TDA-1 is combined with 2,4, 6-tribromophenol (860 grams, 2.6 moles) and sodium carbonate (180 grams, 1.7 moles) in a 3-liter reactor equipped with mechanical stirrer and Dean-Stark trap. The mixture is heated to 130oC and held for five hours.
- 2,4, 6-tribromophenol 860 grams, 2.6 moles
- sodium carbonate 180 grams, 1.7 moles
- Step I 2,4,6-Tribromophenol (1,160 grams, 3.5 moles), lithium hydroxide monohydrate (7.5 grams), and ethylene glycol (2000 grams) are combined in a 5-liter reactor equipped with mechanical stirrer and subsurface gas inlet tube. The mixture is heated to 120oC and ethylene oxide is introduced subsurface at a rate of three to four grams per minute with vigorous stirring. The pH of the reaction mixture is monitored with dampened pH indicator paper.
- Step II Product from Step I (940 grams, 2.5 moles), and pyridine (3 liters) are combined in a 5-liter reactor equipped with mechanical stirrer. After cooling the mixture to ⁇ 5oC, benzenesulfonyl chloride (883 grams, 5 moles) is added dropwise over one hour while keeping the temperature at ⁇ 5oC. The mixture is allowed to slowly warm to room
- Step III Same as Step II of Example 1 except ⁇ -(2,4,6-tribromophenoxy)-ethyl benzenesulfonate (1,160 grams, 2.25 moles) is used in place of
- a flame retardant composition was prepared by blending 20.0 parts halogenated unsymmetrical higher alkyl bisphenoxy alkane (Compound A); 69.0 parts ABS resin, which is available from Borg-Warner
- chlorinated polyethylene which is available from The Dow Chemical Company as TYRIN CPE-4213S; 5.0 parts antimony trioxide, which is available from M & T Chemical Company as THERMOGUARD S; 0.5 parts stabilizer, which is available from Ciba Geigy
- antioxidant which is available from Ciba Geigy Corporation as Irganox 1076.
- Compound A is 1-(tribromophenoxy)- 2-(dibromononyIphenoxy)-ethane, a halogenated unsymmetrical higher alkyl bisphenoxy alkane
- the resultant mixture was blended in a
- Flame retardant compositions were prepared using the method of Example 5 , except that Compound A was replaced by Compound J, Compound F, Compound K, and Compound L, respectively in a proportion so as to maintain a 10.8 percent by weight bromine concentration in the resulting polymer composition. Identity for these Compounds J, F, K, and L are listed in Table III.
- Table IV shows the results of the experimental evaluations of various test specimens and may be summarized as follows.
- Example 5 illustrates a flame retardant ABS formulation incorporating halogenated unsymmetrical higher alkyl bisphenoxy alkane in accordance with this invention. A flammability rating of V-O was achieved, and bloom was not observed.
- Comparative Examples 1-4 show that prior art symmetrical bisphenoxy compound, when used in V-O formulation, migrate (bloom) from ABS resin.
- Examples 6-11 illustrate flame retardant formulations incorporating other halogenated
- ABS resins incorporating halogenated unsymmetrical higher alkyl bisphenoxy alkanes of this invention do not bloom whereas symmetrical bisphenoxy alkanes do bloom or tend to migrate from the resin
- ABS resins incorporating the halogenated unsymmetrical higher alkyl bisphenoxy alkanes of this invention exhibit excellent resistance to light instability, to thermal migration of flame retarding agents, and have improved physical properties, such as impact strength and tensile elongation.
- Flame retardant compositions were prepared using the method of Example 5, except that Compound A was partially replaced by Compound J in proportion as specified in Table V, so as to maintain a constant weight of bromine-containing flame retardant.
- a flame retardant composition was prepared using the method of Example 5, except that Compound A was replaced by Compound J in proportion as specified in Table V.
- Table V shows the results of experimental evaluation of the various test specimens and may be summarized as follows:
- Example 5 Example 5
- Examples 12-14 show no evidence of bloom in compositions comprising mixtures of the agents of this invention with bis(tribromophenoxy)-ethane (Compound J).
- Compound J bis(tribromophenoxy)-ethane
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019900700438A KR900701715A (en) | 1988-06-30 | 1989-06-29 | Flame retardant ABS resin composition and its use for ABS polymer system |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/213,540 US4891449A (en) | 1988-06-30 | 1988-06-30 | Halogenated unsymmetrical higher alkyl phenoxy alkanes |
US07/213,538 US4880862A (en) | 1988-06-30 | 1988-06-30 | Flame retardant ABS resin composition |
US213,538 | 1988-06-30 | ||
US213,540 | 1988-06-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1990000165A1 true WO1990000165A1 (en) | 1990-01-11 |
Family
ID=26908171
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1989/002796 WO1990000165A1 (en) | 1988-06-30 | 1989-06-29 | Flame retardant higher alkyl bisphenoxy alkanes and their application to abs polymer systems |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0388445A4 (en) |
JP (1) | JPH03503419A (en) |
KR (1) | KR900701715A (en) |
CA (1) | CA1317603C (en) |
WO (1) | WO1990000165A1 (en) |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3660351A (en) * | 1970-03-12 | 1972-05-02 | American Cyanamid Co | Flame resistant acrylonitrile polymers |
US3876612A (en) * | 1972-06-06 | 1975-04-08 | Michigan Chem Corp | Abs plastic compositions containing bis-phenoxy flame retardants |
US3883479A (en) * | 1972-06-06 | 1975-05-13 | Michigan Chem Corp | ABS plastic compositions containing bio-phenoxy flame retardants |
US3892710A (en) * | 1972-06-06 | 1975-07-01 | Michigan Chem Corp | ABS plastic compositions containing halogenated aryl flame retardants |
US3971758A (en) * | 1972-06-06 | 1976-07-27 | Michigan Chemical Corporation | Plastic compositions containing acrylonitrile-butadiene-styrene polymer and a bis-phenoxy flame retardant |
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 |
US4016137A (en) * | 1972-06-06 | 1977-04-05 | Michigan Chemical Corporation | Plastic compositions |
US4051105A (en) * | 1972-06-06 | 1977-09-27 | Velsicol Chemical Corporation | Plastic compositions |
US4059561A (en) * | 1975-02-07 | 1977-11-22 | Showa Denko Kabushiki Kaisha | Flame-resistant composition containing a norbornene derivative polymer |
US4171330A (en) * | 1977-01-27 | 1979-10-16 | Unitika Ltd. | Fire-retardant resin composition |
US4567218A (en) * | 1984-02-01 | 1986-01-28 | Great Lakes Chemical Corporation | Halogenated bisphenol A ether flame retardant for ABS polymers |
-
1989
- 1989-06-28 CA CA000604225A patent/CA1317603C/en not_active Expired - Fee Related
- 1989-06-29 JP JP1507424A patent/JPH03503419A/en active Pending
- 1989-06-29 KR KR1019900700438A patent/KR900701715A/en not_active Ceased
- 1989-06-29 EP EP19890907957 patent/EP0388445A4/en not_active Ceased
- 1989-06-29 WO PCT/US1989/002796 patent/WO1990000165A1/en not_active Application Discontinuation
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3660351A (en) * | 1970-03-12 | 1972-05-02 | American Cyanamid Co | Flame resistant acrylonitrile polymers |
US3876612A (en) * | 1972-06-06 | 1975-04-08 | Michigan Chem Corp | Abs plastic compositions containing bis-phenoxy flame retardants |
US3883479A (en) * | 1972-06-06 | 1975-05-13 | Michigan Chem Corp | ABS plastic compositions containing bio-phenoxy flame retardants |
US3892710A (en) * | 1972-06-06 | 1975-07-01 | Michigan Chem Corp | ABS plastic compositions containing halogenated aryl flame retardants |
US3971758A (en) * | 1972-06-06 | 1976-07-27 | Michigan Chemical Corporation | Plastic compositions containing acrylonitrile-butadiene-styrene polymer and a bis-phenoxy flame retardant |
US4016137A (en) * | 1972-06-06 | 1977-04-05 | Michigan Chemical Corporation | Plastic compositions |
US4051105A (en) * | 1972-06-06 | 1977-09-27 | Velsicol Chemical Corporation | Plastic compositions |
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 |
US4059561A (en) * | 1975-02-07 | 1977-11-22 | Showa Denko Kabushiki Kaisha | Flame-resistant composition containing a norbornene derivative polymer |
US4171330A (en) * | 1977-01-27 | 1979-10-16 | Unitika Ltd. | Fire-retardant resin composition |
US4567218A (en) * | 1984-02-01 | 1986-01-28 | Great Lakes Chemical Corporation | Halogenated bisphenol A ether flame retardant for ABS polymers |
Non-Patent Citations (1)
Title |
---|
See also references of EP0388445A4 * |
Also Published As
Publication number | Publication date |
---|---|
EP0388445A1 (en) | 1990-09-26 |
KR900701715A (en) | 1990-12-04 |
JPH03503419A (en) | 1991-08-01 |
EP0388445A4 (en) | 1991-07-03 |
CA1317603C (en) | 1993-05-11 |
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