CA2309203C - Procede de preparation de polystyrene brome dote de caracteristiques de couleur ameliorees - Google Patents
Procede de preparation de polystyrene brome dote de caracteristiques de couleur ameliorees Download PDFInfo
- Publication number
- CA2309203C CA2309203C CA002309203A CA2309203A CA2309203C CA 2309203 C CA2309203 C CA 2309203C CA 002309203 A CA002309203 A CA 002309203A CA 2309203 A CA2309203 A CA 2309203A CA 2309203 C CA2309203 C CA 2309203C
- Authority
- CA
- Canada
- Prior art keywords
- polystyrene
- weight
- range
- catalyst
- bromine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000004793 Polystyrene Substances 0.000 title claims abstract description 129
- 229920002223 polystyrene Polymers 0.000 title claims abstract description 129
- 238000000034 method Methods 0.000 title claims abstract description 73
- 230000008569 process Effects 0.000 title claims abstract description 59
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 239000003054 catalyst Substances 0.000 claims abstract description 60
- 238000006243 chemical reaction Methods 0.000 claims abstract description 56
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 53
- 238000005893 bromination reaction Methods 0.000 claims abstract description 48
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 48
- 230000031709 bromination Effects 0.000 claims abstract description 46
- 239000002904 solvent Substances 0.000 claims abstract description 44
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 40
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000376 reactant Substances 0.000 claims abstract description 36
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 claims abstract description 31
- 229920000642 polymer Polymers 0.000 claims abstract description 14
- 239000002841 Lewis acid Substances 0.000 claims abstract description 10
- 150000008282 halocarbons Chemical class 0.000 claims abstract description 10
- 230000035484 reaction time Effects 0.000 claims abstract description 10
- 150000007517 lewis acids Chemical class 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims description 47
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 229910001868 water Inorganic materials 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 239000011968 lewis acid catalyst Substances 0.000 claims description 16
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 14
- -1 alkali metal bisulfite Chemical class 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- DAMJCWMGELCIMI-UHFFFAOYSA-N benzyl n-(2-oxopyrrolidin-3-yl)carbamate Chemical group C=1C=CC=CC=1COC(=O)NC1CCNC1=O DAMJCWMGELCIMI-UHFFFAOYSA-N 0.000 claims description 10
- 238000009835 boiling Methods 0.000 claims description 10
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 239000002002 slurry Substances 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 4
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 3
- RPJGYLSSECYURW-UHFFFAOYSA-K antimony(3+);tribromide Chemical group Br[Sb](Br)Br RPJGYLSSECYURW-UHFFFAOYSA-K 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 241000284466 Antarctothoa delta Species 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims 1
- 238000010791 quenching Methods 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 18
- 230000000996 additive effect Effects 0.000 abstract description 14
- 238000002955 isolation Methods 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 4
- 230000029936 alkylation Effects 0.000 abstract description 2
- 238000005804 alkylation reaction Methods 0.000 abstract description 2
- 230000006872 improvement Effects 0.000 abstract description 2
- 230000001939 inductive effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 13
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 12
- 239000003063 flame retardant Substances 0.000 description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000003086 colorant Substances 0.000 description 6
- 229920001169 thermoplastic Polymers 0.000 description 6
- 239000004416 thermosoftening plastic Substances 0.000 description 6
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- JVPKLOPETWVKQD-UHFFFAOYSA-N 1,2,2-tribromoethenylbenzene Chemical compound BrC(Br)=C(Br)C1=CC=CC=C1 JVPKLOPETWVKQD-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000026030 halogenation Effects 0.000 description 3
- 238000005658 halogenation reaction Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- CYLVUSZHVURAOY-UHFFFAOYSA-N 2,2-dibromoethenylbenzene Chemical compound BrC(Br)=CC1=CC=CC=C1 CYLVUSZHVURAOY-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- FBAFATDZDUQKNH-UHFFFAOYSA-M iron chloride Chemical compound [Cl-].[Fe] FBAFATDZDUQKNH-UHFFFAOYSA-M 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012778 molding material Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- ZFYXTBYFHIVKEC-UHFFFAOYSA-N 1,2,4-tribromo-5-ethenylbenzene Chemical compound BrC1=CC(Br)=C(C=C)C=C1Br ZFYXTBYFHIVKEC-UHFFFAOYSA-N 0.000 description 1
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
- 101100437861 Caenorhabditis elegans brc-1 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001596 poly (chlorostyrenes) Polymers 0.000 description 1
- 229920000314 poly p-methyl styrene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011027 product recovery Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
L'invention se rapporte à un procédé de préparation de polystyrène bromé utilisé comme additif permettant de conférer à des matrices polymères un pouvoir ignifuge. Ce procédé consiste à préparer une solution d'un réactif à base de polystyrène contenant approximativement 5 à 20 % en poids d'un réactif à base de polystyrène, dans un solvant hydrocarboné halogéné; à ajouter un catalyseur de bromation à base d'acide de Lewis de façon à former une solution; à ajouter à la solution de 1 mole environ à 3,3 moles environ d'un agent de bromation, par mole de motifs répétitifs de polystyrène, et à faire réagir le réactif à base de polystyrène avec l'agent de bromation, à une température comprise approximativement entre -20 DEG C et 50 DEG C. Le perfectionnement du procédé réside dans un contrôle des caractéristiques de couleur du polystyrène bromé résultant. Pour ce faire, on sélectionne un réactif à base de polystyrène ayant un poids moléculaire moyen en poids compris approximativement entre 500 et 1 500 000; on sélectionne une quantité catalytiquement active du catalyseur, c'est à dire possédant une force suffisante pour effectuer au moins une monobromation du polystyrène sans induire l'alkylation du polystyrène par le solvant hydrocarboné halogéné; on sélectionne un agent de bromation dans le groupe constitué par le chlorure de brome et le brome; on procède à la température la plus faible possible, compatible avec l'agent de bromation et le catalyseur sélectionné; et l'on isole le polystyrène bromé, dont les caractéristiques de couleur ont été améliorées grâce à l'étude et à la sélection de la durée et de la température de réaction, du catalyseur, de l'agent de bromation et du procédé d'isolement du produit.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1997/021240 WO1999025746A1 (fr) | 1996-06-14 | 1997-11-18 | Procede de preparation de polystyrene brome dote de caracteristiques de couleur ameliorees |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2309203A1 CA2309203A1 (fr) | 1999-05-27 |
| CA2309203C true CA2309203C (fr) | 2007-07-03 |
Family
ID=22262107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002309203A Expired - Fee Related CA2309203C (fr) | 1997-11-18 | 1997-11-18 | Procede de preparation de polystyrene brome dote de caracteristiques de couleur ameliorees |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4109417B2 (fr) |
| AU (1) | AU5449998A (fr) |
| CA (1) | CA2309203C (fr) |
| DE (1) | DE69739318D1 (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0614223A2 (pt) * | 2005-06-30 | 2011-03-15 | Albemarle Corp | polìmeros estirênicos bromados e suas preparações |
| CN117247482B (zh) * | 2023-11-17 | 2024-02-20 | 山东旭锐新材股份有限公司 | 一种高热稳定性溴化聚苯乙烯合成方法 |
-
1997
- 1997-11-18 JP JP2000521125A patent/JP4109417B2/ja not_active Expired - Fee Related
- 1997-11-18 DE DE69739318T patent/DE69739318D1/de not_active Expired - Lifetime
- 1997-11-18 CA CA002309203A patent/CA2309203C/fr not_active Expired - Fee Related
- 1997-11-18 AU AU54499/98A patent/AU5449998A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE69739318D1 (de) | 2009-04-30 |
| JP4109417B2 (ja) | 2008-07-02 |
| CA2309203A1 (fr) | 1999-05-27 |
| AU5449998A (en) | 1999-06-07 |
| JP2001523738A (ja) | 2001-11-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20151118 |