CA2743025A1 - Bromination of telomer mixtures derived from toluene and styrene - Google Patents
Bromination of telomer mixtures derived from toluene and styrene Download PDFInfo
- Publication number
- CA2743025A1 CA2743025A1 CA2743025A CA2743025A CA2743025A1 CA 2743025 A1 CA2743025 A1 CA 2743025A1 CA 2743025 A CA2743025 A CA 2743025A CA 2743025 A CA2743025 A CA 2743025A CA 2743025 A1 CA2743025 A1 CA 2743025A1
- Authority
- CA
- Canada
- Prior art keywords
- molecules
- distribution
- bromine
- gpc area
- telomer
- 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
- 238000005893 bromination reaction Methods 0.000 title claims description 54
- 230000031709 bromination Effects 0.000 title claims description 48
- 239000000203 mixture Substances 0.000 title claims description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 title abstract description 128
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 title abstract description 62
- 238000009826 distribution Methods 0.000 claims abstract description 85
- 229910052794 bromium Inorganic materials 0.000 claims description 105
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 103
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 65
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- 230000008569 process Effects 0.000 claims description 47
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
- 229910001868 water Inorganic materials 0.000 claims description 38
- 239000002002 slurry Substances 0.000 claims description 26
- 239000012279 sodium borohydride Substances 0.000 claims description 23
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 23
- 239000003795 chemical substances by application Substances 0.000 claims description 22
- 239000012071 phase Substances 0.000 claims description 20
- 238000010791 quenching Methods 0.000 claims description 19
- 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 class 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 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 15
- 239000008346 aqueous phase Substances 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- FNXLCIKXHOPCKH-UHFFFAOYSA-N bromamine Chemical class BrN FNXLCIKXHOPCKH-UHFFFAOYSA-N 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 238000010533 azeotropic distillation Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 238000001556 precipitation Methods 0.000 claims description 4
- 230000000171 quenching effect Effects 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 3
- 239000012298 atmosphere Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000013505 freshwater Substances 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- 239000012265 solid product Substances 0.000 claims 2
- 239000003063 flame retardant Substances 0.000 abstract description 25
- 239000000758 substrate Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 60
- 239000000243 solution Substances 0.000 description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 238000004458 analytical method Methods 0.000 description 21
- 239000000047 product Substances 0.000 description 21
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 21
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 17
- 238000012546 transfer Methods 0.000 description 15
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 13
- 239000011521 glass Substances 0.000 description 13
- -1 poly(tertiary amines) Polymers 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- 238000001816 cooling Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 239000000178 monomer Substances 0.000 description 11
- 229920001577 copolymer Polymers 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000013019 agitation Methods 0.000 description 9
- 239000000306 component Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 239000004810 polytetrafluoroethylene Substances 0.000 description 9
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- 229920000642 polymer Polymers 0.000 description 8
- 241000894007 species Species 0.000 description 8
- VEAFKIYNHVBNIP-UHFFFAOYSA-N 1,3-Diphenylpropane Chemical compound C=1C=CC=CC=1CCCC1=CC=CC=C1 VEAFKIYNHVBNIP-UHFFFAOYSA-N 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 7
- 239000003518 caustics Substances 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 229920001169 thermoplastic Polymers 0.000 description 7
- YYLMGEBQHHVBAN-UHFFFAOYSA-N 1,5-diphenylpentan-3-ylbenzene Chemical compound C=1C=CC=CC=1CCC(C=1C=CC=CC=1)CCC1=CC=CC=C1 YYLMGEBQHHVBAN-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 125000000129 anionic group Chemical group 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000000376 reactant Substances 0.000 description 6
- 239000004416 thermosoftening plastic Substances 0.000 description 6
- FKLHPAQZDKDOPI-UHFFFAOYSA-N 1,5,7-triphenylheptan-3-ylbenzene Chemical compound C=1C=CC=CC=1CCC(C=1C=CC=CC=1)CC(C=1C=CC=CC=1)CCC1=CC=CC=C1 FKLHPAQZDKDOPI-UHFFFAOYSA-N 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 239000012986 chain transfer agent Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000008399 tap water Substances 0.000 description 5
- 235000020679 tap water Nutrition 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- BDNXSMXBSABNSH-UHFFFAOYSA-N 1,3,7,9-tetraphenylnonan-5-ylbenzene Chemical compound C=1C=CC=CC=1CCC(C=1C=CC=CC=1)CC(C=1C=CC=CC=1)CC(C=1C=CC=CC=1)CCC1=CC=CC=C1 BDNXSMXBSABNSH-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 4
- 238000002485 combustion reaction Methods 0.000 description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- 230000002572 peristaltic effect Effects 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 238000003809 water extraction Methods 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 3
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- HAUKUGBTJXWQMF-UHFFFAOYSA-N lithium;propan-2-olate Chemical class [Li+].CC(C)[O-] HAUKUGBTJXWQMF-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000012963 UV stabilizer Substances 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- PQLAYKMGZDUDLQ-UHFFFAOYSA-K aluminium bromide Chemical compound Br[Al](Br)Br PQLAYKMGZDUDLQ-UHFFFAOYSA-K 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 230000017525 heat dissipation Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical class BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000010943 off-gassing Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- QXSZNDIIPUOQMB-UHFFFAOYSA-N 1,1,2,2-tetrabromoethane Chemical compound BrC(Br)C(Br)Br QXSZNDIIPUOQMB-UHFFFAOYSA-N 0.000 description 1
- QUMDOMSJJIFTCA-UHFFFAOYSA-N 1,1,2-tribromoethane Chemical compound BrCC(Br)Br QUMDOMSJJIFTCA-UHFFFAOYSA-N 0.000 description 1
- APQIUTYORBAGEZ-UHFFFAOYSA-N 1,1-dibromoethane Chemical compound CC(Br)Br APQIUTYORBAGEZ-UHFFFAOYSA-N 0.000 description 1
- BZQKBFHEWDPQHD-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[2-(2,3,4,5,6-pentabromophenyl)ethyl]benzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1CCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br BZQKBFHEWDPQHD-UHFFFAOYSA-N 0.000 description 1
- XFNJYAKDBJUJAJ-UHFFFAOYSA-N 1,2-dibromopropane Chemical compound CC(Br)CBr XFNJYAKDBJUJAJ-UHFFFAOYSA-N 0.000 description 1
- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 1
- XKVLZBNEPALHIO-UHFFFAOYSA-N 1-bromo-2-methylbutane Chemical compound CCC(C)CBr XKVLZBNEPALHIO-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001347 alkyl bromides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000010936 aqueous wash Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000000071 blow moulding Methods 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- XNNQFQFUQLJSQT-UHFFFAOYSA-N bromo(trichloro)methane Chemical compound ClC(Cl)(Cl)Br XNNQFQFUQLJSQT-UHFFFAOYSA-N 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009841 combustion method Methods 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000003872 feeding technique Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000012432 intermediate storage Methods 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 235000010333 potassium nitrate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- RKSOPLXZQNSWAS-UHFFFAOYSA-N tert-butyl bromide Chemical compound CC(C)(C)Br RKSOPLXZQNSWAS-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
- C07C17/12—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms in the ring of aromatic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/06—Hydrocarbons
- C08F12/08—Styrene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
- C08F8/22—Halogenation by reaction with free halogens
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/08—Organic materials containing halogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/14—Macromolecular materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Fireproofing Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11927608P | 2008-12-02 | 2008-12-02 | |
| US61/119,276 | 2008-12-02 | ||
| PCT/US2009/066127 WO2010065464A1 (en) | 2008-12-02 | 2009-11-30 | Bromination of telomer mixtures derived from toluene and styrene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2743025A1 true CA2743025A1 (en) | 2010-06-10 |
Family
ID=41647217
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2743025A Abandoned CA2743025A1 (en) | 2008-12-02 | 2009-11-30 | Bromination of telomer mixtures derived from toluene and styrene |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8642821B2 (enExample) |
| EP (1) | EP2373697A1 (enExample) |
| JP (1) | JP2012510539A (enExample) |
| KR (1) | KR20110103942A (enExample) |
| CN (1) | CN102232089B (enExample) |
| CA (1) | CA2743025A1 (enExample) |
| IL (1) | IL213274A0 (enExample) |
| MX (1) | MX2011005661A (enExample) |
| TW (1) | TW201030037A (enExample) |
| WO (1) | WO2010065464A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG184732A1 (en) | 2007-06-07 | 2012-10-30 | Albemarle Corp | Low molecular weight brominated polymers and their use in thermoplastic formulations |
| US8993684B2 (en) | 2008-06-06 | 2015-03-31 | Albemarle Corporation | Low molecular weight brominated polymers, processes for their manufacture and their use in thermoplastic formulations |
| JO3423B1 (ar) | 2008-12-02 | 2019-10-20 | Albemarle Corp | مؤخرات لهب معالجة بالبروم و مواد مشتقه منها |
| TW201029955A (en) | 2008-12-02 | 2010-08-16 | Albemarle Corp | Toluene and styrene derived telomer distributions and brominated flame retardants produced therefrom |
| WO2010065464A1 (en) | 2008-12-02 | 2010-06-10 | Albemarle Corporation | Bromination of telomer mixtures derived from toluene and styrene |
| EP2479210A1 (en) | 2008-12-02 | 2012-07-25 | Albemarle Corporation | Branched and star-branched styrene polymers, telomers, and adducts, their synthesis, their bromination, and their uses |
| TW201043651A (en) | 2009-05-01 | 2010-12-16 | Albemarle Corp | Pelletized low molecular weight brominated aromatic polymer compositions |
| JO3059B1 (ar) | 2009-05-01 | 2017-03-15 | Albemarle Corp | معالجة بالبروم لتراكيب بوليمرات عطرية ذات وزن جزيئي منخفض |
| KR20250157422A (ko) | 2023-03-06 | 2025-11-04 | 란세스 코포레이션 | 데카브로모디페닐 에탄-무함유 난연성 열가소성 조성물 |
Family Cites Families (127)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2243543A (en) | 1938-10-14 | 1941-05-27 | Us Rubber Co | Parasiticide |
| US2757146A (en) | 1952-09-08 | 1956-07-31 | Du Pont | Pyrolysis polymers from p-methyl quaternary benzylammonium hydroxides |
| US2914489A (en) | 1956-01-10 | 1959-11-24 | Du Pont | Production of poly p-xylene polymers containing halogen |
| US2954412A (en) | 1957-01-10 | 1960-09-27 | Huels Chemische Werke Ag | Process for the preparation of dibenzylbenzenes |
| US3221068A (en) | 1962-03-01 | 1965-11-30 | Union Carbide Corp | Halogenated di-p-xylylenes |
| US3541149A (en) | 1963-03-13 | 1970-11-17 | Exxon Research Engineering Co | Crystalline organolithium-tertiary chelating polyamine complexes |
| US3594396A (en) | 1963-03-13 | 1971-07-20 | Arthur W Langer Jr | Crystalline organolithium complexes containing silicon |
| US3751384A (en) | 1963-03-13 | 1973-08-07 | Exxon | Organolithium-polyamine compositions |
| US3458586A (en) | 1964-04-13 | 1969-07-29 | Exxon Research Engineering Co | Linear alkyl aromatic compounds and their preparation |
| US3373135A (en) | 1964-12-01 | 1968-03-12 | Kalk Chemische Fabrik Gmbh | Shaped articles of self-extinguishing epoxy resins |
| NL126613C (enExample) | 1966-03-25 | |||
| US3372880A (en) | 1966-04-14 | 1968-03-12 | Rexall Drug Chemical | Process for the production of polymer powder |
| US3451988A (en) | 1966-10-25 | 1969-06-24 | Exxon Research Engineering Co | Polymerization catalyst and uses thereof |
| GB1174845A (en) | 1967-08-25 | 1969-12-17 | Shell Int Research | The Polymerisation of Vinyl-Aromatic Compounds, and the Resulting Polyvinyl-Aromatic Compounds |
| DE1589700A1 (de) | 1967-11-03 | 1970-07-23 | Delma Gmbh | Hochfrequenz-Generator fuer die Elektrochirurgie |
| DE1794072C3 (de) | 1968-09-03 | 1975-09-25 | Basf Ag, 6700 Ludwigshafen | Schwerbrennbare Formmassen auf der Basis von Polymerisaten des Propylene |
| GB1288057A (enExample) * | 1968-11-26 | 1972-09-06 | ||
| GB1051269A (enExample) | 1969-05-16 | |||
| US3634548A (en) | 1969-08-11 | 1972-01-11 | Gulf Research Development Co | Polystyrene-ethylene graft copolymer |
| BE757383A (fr) | 1969-10-13 | 1971-04-13 | Phillips Petroleum Co | Compositions ignifuges et systemes d'additifs pour celles-ci |
| US3751501A (en) | 1970-01-15 | 1973-08-07 | Lithium Corp | Telomerization reactions utilizing liquid hydrocarbon solutions of certain organometallic complexes |
| DE2063643A1 (de) | 1970-01-15 | 1971-07-29 | Lithium Corp Of Ameria | Telomensationsreaktionen unter Ver wendung von flussigen Kohlenwasserstoff lösungen bestimmter metallorganischer Ver bindungen |
| US3668263A (en) | 1970-01-19 | 1972-06-06 | Lithium Corp | Organolithium polymerization initiators and use thereof in polymerization processes |
| US3725368A (en) | 1970-01-19 | 1973-04-03 | Lithium Corp | Preparation of polymers |
| US3742077A (en) | 1970-07-23 | 1973-06-26 | Lithium Corp | Method of preparing telomers utilizing as catalysts hydrocarbon-soluble organometallic complexes of metals of groups i and iia of the periodic table |
| US3850882A (en) | 1971-12-01 | 1974-11-26 | Phillips Petroleum Co | Flame retarded compositions and additive systems therefor |
| US4078019A (en) | 1972-11-24 | 1978-03-07 | Exxon Research & Engineering Co. | Process for polymer lithiation in graft polymerization |
| IT1025744B (it) | 1973-11-26 | 1978-08-30 | Basf Ag | Masse per formatura termopla stiche autoestinglenti |
| US4129705A (en) | 1975-02-02 | 1978-12-12 | Compagnie Generale Des Etablissements Michelin | Polymerization process |
| US4108921A (en) | 1975-03-28 | 1978-08-22 | Exxon Research & Engineering Co. | Process for polymer lithiation in graft polymerization |
| DE2515473C3 (de) | 1975-04-09 | 1987-01-22 | Basf Ag, 6700 Ludwigshafen | Flammwidrige, lineare Polyester |
| CA1054161A (en) * | 1975-08-22 | 1979-05-08 | Herbert Naarmann | Manufacture of heat-stable brominated oligomers of monovinyl-aromatic compounds |
| DE2547498A1 (de) | 1975-10-23 | 1977-04-28 | Huels Chemische Werke Ag | Flammwidrige formmasse |
| US4311818A (en) | 1976-06-17 | 1982-01-19 | Societe Chimique Des Charbonnages-Cdf. Chimie | Bi- and Trifunctional organolithium initiators and applications thereof |
| US4134938A (en) | 1976-08-12 | 1979-01-16 | Exxon Research & Engineering Co. | Process for polymer lithiation in graft polymerization |
| DE2645711C3 (de) | 1976-10-09 | 1979-06-07 | Basf Ag, 6700 Ludwigshafen | Halogenhaltige Flammschutzmittel enthaltende Fasern und Fäden aus linearen, thermoplastischen Polyestern |
| US4041088A (en) | 1976-11-08 | 1977-08-09 | Lithium Corporation Of America | Recirculation telomerization process and its liquid telomers and liquid telomers produced thereby |
| DE2651435C3 (de) | 1976-11-11 | 1980-11-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur Herstellung von bromierten Polymerisationsprodukten des Styrols |
| DE2703419B1 (de) | 1977-01-28 | 1978-02-02 | Basf Ag | Flammwidrig ausgeruestete polyamid- formmassen |
| DE2727483A1 (de) | 1977-06-18 | 1979-01-11 | Basf Ag | Selbstverloeschende thermoplastische formmassen |
| DE2756375A1 (de) | 1977-12-17 | 1979-07-05 | Basf Ag | Flammschutzmittelkonzentrat fuer thermoplaste |
| DE2758781A1 (de) | 1977-12-29 | 1979-07-12 | Basf Ag | Kernhalogenierte poly(benzylene) |
| DE3006448A1 (de) | 1980-02-21 | 1981-08-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von mischungen aus bromierten polystyrolen und bromierten aromatischen verbindungen |
| US4268705A (en) | 1980-03-21 | 1981-05-19 | Phillips Petroleum Company | Addition of monomer in production of liquid polymers |
| JPS5919577B2 (ja) | 1980-08-25 | 1984-05-07 | 日本エラストマ−株式会社 | 耐衝撃性ポリスチレンの製造方法 |
| FR2498193B1 (fr) | 1981-01-19 | 1986-03-21 | Poudres & Explosifs Ste Nale | Nouvelles associations de bases resultant de la combinaison d'un alkyl ou aryl lithien avec un amidure ou un hydrure alcalin, procede de polymerisation les utilisant et produit obtenu |
| IT1195303B (it) | 1981-12-22 | 1988-10-12 | Anic Spa | Iniziatori anionici multifunzionali e loro impiego |
| US4463135A (en) | 1982-10-25 | 1984-07-31 | The Goodyear Tire & Rubber Company | Process for the functionalization of polystyrene resins |
| IT1186743B (it) | 1985-07-01 | 1987-12-16 | Eniricerche Spa | Metodo per la terminazione di polimeri ottenuti per polimerizzazione anionica di monomeri dienici e/o vinilaromatici e composti adatti allo scopo |
| IT1206738B (it) | 1985-07-01 | 1989-05-03 | Eniricerche Spa | Metodo per la terminazione di polimeri viventi ottenuti per polimerizzazione anionica di monomeri dienici e/o vinilaromatici e composti adatti allo scopo. |
| US4636540A (en) | 1985-07-08 | 1987-01-13 | Atlantic Richfield Company | Purification of polymer solutions |
| US4755573A (en) | 1985-11-15 | 1988-07-05 | General Electric Company | Cationic polymerization of bromoalkenyl aromatic compounds with aromatic chain transfer agent, and products |
| US4753745A (en) | 1985-12-30 | 1988-06-28 | The Lubrizol Corporation | Methylene linked aromatic pour point depressant |
| IT1213077B (it) | 1986-06-05 | 1989-12-07 | Eniricerche Spa | Composti stabilizzanti polimerici e procedimento per la loro preparazione. |
| DE3779747T2 (de) | 1987-01-28 | 1993-01-07 | Great Lakes Chemical Corp | Aromatische bromierung von polystyrol mit einer bromverbindung als reaktionsloesungsmittel. |
| US4883846A (en) | 1987-04-20 | 1989-11-28 | The Dow Chemical Company | Anionic polymerization of purified monovinylidene aromatic monomer feed stock |
| US4829135A (en) | 1987-12-29 | 1989-05-09 | Mobil Oil Corporation | Multi-stage anionic dispersion homopolymerization to form microparticles with narrow size distribution |
| FR2629085B1 (fr) | 1988-03-24 | 1992-09-04 | Atochem | Procede de fabrication de polybutadiene et preparation de resine vinylaromatique choc a partir de polybutadiene |
| AU5833890A (en) | 1989-06-06 | 1991-01-07 | Ferro Corporation | High impact polystyrene containing low molecular weight brominated polystyrene |
| US5112897A (en) | 1989-06-06 | 1992-05-12 | Ferro Corporation | High impact polystyrene containing low molecular weight brominated polystyrene |
| US5112898A (en) | 1989-06-06 | 1992-05-12 | Ferro Corporation | High impact polystyrene containing low molecular weight brominated polystyrene |
| US4975496A (en) | 1989-08-10 | 1990-12-04 | The Dow Chemical Company | Process for brominating aromatic resins |
| US4950721A (en) | 1989-10-03 | 1990-08-21 | Exxon Chemical Patents Inc. | Ion-exchange reactions for polymeric alkali metal carboxylates |
| CA2047256C (en) | 1990-07-30 | 2002-03-05 | Saadat Hussain | Process for decabromodiphenylalkane predominant product |
| KR940003782B1 (ko) | 1991-09-03 | 1994-05-03 | 주식회사 럭키 | 스티렌계 난연수지의 제조방법 |
| US5196622A (en) | 1991-11-22 | 1993-03-23 | Phillips Petroleum Company | Alkene addition process |
| US5198594A (en) | 1991-11-27 | 1993-03-30 | Amoco Corporation | Alkylation of alkylaromatics promoted by sonicated alkali metal |
| EP0554675A1 (de) | 1992-01-31 | 1993-08-11 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von Polymeren des para-Xylylens und von diesem abgeleiteten Derivaten |
| US6025450A (en) | 1992-10-02 | 2000-02-15 | Bridgestone Corporation | Amine containing polymers and products therefrom |
| US5625017A (en) | 1992-10-19 | 1997-04-29 | Bridgestone Corporation | Process for preparing a polymer using lithium initiator prepared by in situ preparation |
| DE69413217T2 (de) | 1993-04-07 | 1999-02-18 | Great Lakes Chemical Corp., West Lafayette, Ind. | Bromierte diphenylalkane und verfahren |
| US5687090A (en) | 1994-09-01 | 1997-11-11 | Aspen Technology, Inc. | Polymer component characterization method and process simulation apparatus |
| EP0784648B2 (en) | 1994-10-05 | 2010-10-27 | Great Lakes Chemical Corporation | Continuous bromination process and products thereof |
| DE19516563A1 (de) | 1995-05-05 | 1996-11-07 | Basf Ag | Verfahren zur Herstellung von Styrol-Oligomeren und deren Verwendung als Schmiermittel in Thermoplasten |
| US5534592A (en) | 1995-09-22 | 1996-07-09 | The Goodyear Tire & Rubber Company | High performance blend for tire treads |
| CA2190302A1 (en) | 1995-11-22 | 1997-05-23 | Gregory George Smith | Process for preparing vulcanizable elastomeric compounds from granular elastomer blends and elastomeric articles manufactured therefrom |
| DE19618678A1 (de) | 1996-05-09 | 1997-11-13 | Basf Ag | Verfahren zur Herstellung von Polystyrol durch kontinuierliche anionische Polymerisation |
| US5723549A (en) | 1996-06-14 | 1998-03-03 | Ferro Corporation | Process for the preparation of brominated polystyrene having improved color characteristics |
| US5637650A (en) | 1996-06-14 | 1997-06-10 | Ferro Corporation | Brominated polysytrene having improved thermal stability and color and process for the preparation thereof |
| US6518368B2 (en) | 1996-06-14 | 2003-02-11 | Albemarle Corporation | Brominated polystyrene having improved thermal stability and color and process for the preparation thereof |
| US6235844B1 (en) | 1996-09-26 | 2001-05-22 | Albemarle Corporation | Brominated polystyrenic resins |
| US5686538A (en) | 1996-09-26 | 1997-11-11 | Albemarle Corporation | Process for brominating polystyrenic resins |
| EP0928300B1 (en) | 1996-09-26 | 2000-05-10 | Albemarle Corporation | Process for brominated styrenic polymers |
| US5677390A (en) | 1996-09-26 | 1997-10-14 | Albemarle Corporation | Process for brominating polystyrenic resins |
| US5767203A (en) | 1996-09-26 | 1998-06-16 | Albemarle Corporation | Process for brominated styrenic polymers |
| US6133381A (en) | 1996-09-26 | 2000-10-17 | Albelmarle Corporation | Brominated polystyrenic flame retardants |
| US6326439B1 (en) | 1996-09-26 | 2001-12-04 | Albemarle Corporation | Process for brominating polystyrenic resins |
| US6521714B2 (en) | 1996-09-26 | 2003-02-18 | Albemarle Corporation | Brominated polystyrenic resins |
| US6232408B1 (en) | 1996-09-26 | 2001-05-15 | Albemarle Corporation | Brominated polstyrenic resins |
| US6232393B1 (en) | 1996-09-26 | 2001-05-15 | Albemarle Corporation | Polymers flame retarded with brominated polystyrenic resins |
| US6235831B1 (en) | 1996-09-26 | 2001-05-22 | Albemarle Corporation | Polymer compositions containing brominated polystyrenic resins |
| US5728782A (en) | 1996-12-06 | 1998-03-17 | Union Carbide Chemicals & Plastics Technology Corporation | Gas phase anionic polymerization of dienes and vinyl-substituted aromatic compounds |
| KR20000070006A (ko) | 1997-01-08 | 2000-11-25 | 마이클 비. 키한 | 탄화수소 수지 제조용 촉매로서의 플루오르화 고체산 |
| US6008283A (en) | 1997-03-20 | 1999-12-28 | Great Lakes Chemical Corporation | Oligomeric flame retardant additive |
| JPH1143511A (ja) * | 1997-07-30 | 1999-02-16 | Tosoh Corp | 臭素化スチレンオリゴマー、その製造方法、及びそれを配合してなる難燃性樹脂組成物 |
| DE19754504A1 (de) | 1997-12-09 | 1999-06-10 | Basf Ag | Verfahren zur Herstellung von Erdalkalidiorganylverbindungen |
| US6362293B1 (en) | 1998-04-07 | 2002-03-26 | The Dow Chemical Company | Syndiotactic vinylidene aromatic polymerization process |
| US6093211A (en) | 1998-04-09 | 2000-07-25 | Aspen Technology, Inc. | Polymer property distribution functions methodology and simulators |
| KR20000019517A (ko) | 1998-09-12 | 2000-04-15 | 이정국 | 스티렌 다이머 및 스티렌 트리머의 용출이 되지 않는 식품포장재용 고순도 폴리스티렌 및 그의 제조방법 |
| US6821456B2 (en) | 1998-09-22 | 2004-11-23 | Albemarle Corporation | Granular polymer additives and their preparation |
| US6355194B1 (en) | 1999-03-22 | 2002-03-12 | Xerox Corporation | Carrier pelletizing processes |
| US6313230B1 (en) | 1999-09-21 | 2001-11-06 | Industrial Technology Research Institute | Catalyst composition for hydrogenation of conjugated diene based synthetic rubbers |
| US6759498B2 (en) | 2000-05-08 | 2004-07-06 | Asahi Kadei Kabushiki Kaisha | Process for producing styrene resin reduced in content of low-molecular ingredient |
| EP1288260A1 (en) | 2001-08-29 | 2003-03-05 | Albemarle Corporation | Flame retardant compositions |
| DE10218161A1 (de) | 2002-04-23 | 2003-11-13 | Basf Ag | Initiatorzusammensetzung und Verfahren zur anionischen Polymerisation |
| WO2003095499A1 (en) | 2002-05-10 | 2003-11-20 | Ps Japan Corporation | Styrene polymer resin and composition thereof |
| US6657028B1 (en) | 2002-08-01 | 2003-12-02 | Albemarle Corporation | Anionic polymerization process |
| KR100471716B1 (ko) | 2002-08-03 | 2005-03-10 | 금호석유화학 주식회사 | 연속식 음이온 중합에 의한 내충격 비닐 방향족 고분자의제조방법 |
| WO2004113400A2 (en) | 2003-06-20 | 2004-12-29 | Scimed Life Systems, Inc. | End-cappped polymer chains and products thereof |
| US20050209408A1 (en) | 2004-03-17 | 2005-09-22 | Lee Hyung-Jae | Star-shaped polymer, multiple star polymer and their preparation methods |
| WO2005118245A1 (en) | 2004-05-20 | 2005-12-15 | Albemarle Corporation | Pelletized brominated anionic styrenic polymers and their preparation and use |
| ATE453671T1 (de) | 2004-09-30 | 2010-01-15 | Chemtura Corp | Verbesserte bromstyrol-polymere mit kontrolliertem molekülgewicht |
| US7351777B2 (en) | 2005-03-30 | 2008-04-01 | Moore Eugene R | Retarded anionic polymerization of vinyl aromatic monomers using insoluble or heterogeneous retardants |
| CN100369941C (zh) | 2005-05-17 | 2008-02-20 | 北京化工大学 | 一种氢化苯乙烯类热塑性弹性体及其制备方法 |
| MX2007015601A (es) * | 2005-06-30 | 2008-02-25 | Albemarle Corp | Polimeros estirenicos bromados y su preparacion. |
| KR100827335B1 (ko) | 2005-10-06 | 2008-05-06 | 주식회사 엘지화학 | 그라프트 공중합체 및 이의 제조방법 |
| JP5261190B2 (ja) | 2005-12-21 | 2013-08-14 | アルベマール・コーポレーシヨン | 臭素化アニオン性スチレン性ポリマー及びそれらの製造 |
| MX2009005458A (es) | 2006-11-28 | 2009-06-01 | Albemarle Corp | Conversion de polimero estirenico anionico bromado en forma mas dura y larga para almacenamiento, envio y uso. |
| SG184732A1 (en) * | 2007-06-07 | 2012-10-30 | Albemarle Corp | Low molecular weight brominated polymers and their use in thermoplastic formulations |
| MX2010013175A (es) | 2008-06-06 | 2011-02-22 | Albemarle Corp | Polimeros bromados de bajo peso molecular, procesos para su manufactura y su uso en formulaciones termoplasticas. |
| JO3423B1 (ar) | 2008-12-02 | 2019-10-20 | Albemarle Corp | مؤخرات لهب معالجة بالبروم و مواد مشتقه منها |
| WO2010065464A1 (en) | 2008-12-02 | 2010-06-10 | Albemarle Corporation | Bromination of telomer mixtures derived from toluene and styrene |
| EP2479210A1 (en) | 2008-12-02 | 2012-07-25 | Albemarle Corporation | Branched and star-branched styrene polymers, telomers, and adducts, their synthesis, their bromination, and their uses |
| TW201029955A (en) | 2008-12-02 | 2010-08-16 | Albemarle Corp | Toluene and styrene derived telomer distributions and brominated flame retardants produced therefrom |
| TW201043651A (en) | 2009-05-01 | 2010-12-16 | Albemarle Corp | Pelletized low molecular weight brominated aromatic polymer compositions |
| JO3059B1 (ar) | 2009-05-01 | 2017-03-15 | Albemarle Corp | معالجة بالبروم لتراكيب بوليمرات عطرية ذات وزن جزيئي منخفض |
| CA2757889A1 (en) | 2009-05-01 | 2010-11-04 | Albemarle Corporation | Pelletized low molecular weight brominated aromatic polymer compositions |
-
2009
- 2009-11-30 WO PCT/US2009/066127 patent/WO2010065464A1/en not_active Ceased
- 2009-11-30 CA CA2743025A patent/CA2743025A1/en not_active Abandoned
- 2009-11-30 JP JP2011538716A patent/JP2012510539A/ja not_active Ceased
- 2009-11-30 KR KR1020117012473A patent/KR20110103942A/ko not_active Withdrawn
- 2009-11-30 TW TW098140742A patent/TW201030037A/zh unknown
- 2009-11-30 EP EP09764156A patent/EP2373697A1/en not_active Withdrawn
- 2009-11-30 CN CN2009801484061A patent/CN102232089B/zh not_active Expired - Fee Related
- 2009-11-30 US US13/130,101 patent/US8642821B2/en not_active Expired - Fee Related
- 2009-11-30 MX MX2011005661A patent/MX2011005661A/es not_active Application Discontinuation
-
2011
- 2011-05-31 IL IL213274A patent/IL213274A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR20110103942A (ko) | 2011-09-21 |
| CN102232089A (zh) | 2011-11-02 |
| MX2011005661A (es) | 2011-06-16 |
| JP2012510539A (ja) | 2012-05-10 |
| WO2010065464A1 (en) | 2010-06-10 |
| IL213274A0 (en) | 2011-07-31 |
| CN102232089B (zh) | 2013-11-13 |
| US20110224467A1 (en) | 2011-09-15 |
| US8642821B2 (en) | 2014-02-04 |
| TW201030037A (en) | 2010-08-16 |
| EP2373697A1 (en) | 2011-10-12 |
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