DE3337223A1 - Hochbromierte polystyrole, verfahren zu deren herstellung und anwendung - Google Patents
Hochbromierte polystyrole, verfahren zu deren herstellung und anwendungInfo
- Publication number
- DE3337223A1 DE3337223A1 DE19833337223 DE3337223A DE3337223A1 DE 3337223 A1 DE3337223 A1 DE 3337223A1 DE 19833337223 DE19833337223 DE 19833337223 DE 3337223 A DE3337223 A DE 3337223A DE 3337223 A1 DE3337223 A1 DE 3337223A1
- Authority
- DE
- Germany
- Prior art keywords
- solvent
- bromine
- bromide
- highly brominated
- reaction mixture
- 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.)
- Granted
Links
- 239000004793 Polystyrene Substances 0.000 title claims abstract description 23
- 229920002223 polystyrene Polymers 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 16
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000011541 reaction mixture Substances 0.000 claims abstract description 10
- 230000031709 bromination Effects 0.000 claims abstract description 7
- 238000005893 bromination reaction Methods 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims abstract description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 6
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 5
- 230000026030 halogenation Effects 0.000 claims abstract description 4
- 238000005658 halogenation reaction Methods 0.000 claims abstract description 4
- 239000004033 plastic Substances 0.000 claims abstract description 3
- 229920003023 plastic Polymers 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000003063 flame retardant Substances 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000002685 polymerization catalyst Substances 0.000 claims description 5
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 2
- -1 alkyl hydroxide Chemical compound 0.000 claims 1
- 238000002955 isolation Methods 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- BMSUWQXMTMGEOM-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-ethenylbenzene Chemical compound BrC1=C(Br)C(Br)=C(C=C)C(Br)=C1Br BMSUWQXMTMGEOM-UHFFFAOYSA-N 0.000 description 19
- VCKGAEKPOCKYJV-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-(2-bromoethyl)benzene Chemical compound BrCCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br VCKGAEKPOCKYJV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 229920001169 thermoplastic Polymers 0.000 description 5
- 239000004416 thermosoftening plastic Substances 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-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
- 239000012074 organic phase Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003440 styrenes Chemical class 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
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/16—Halogens
- C08F12/18—Chlorine
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833337223 DE3337223A1 (de) | 1983-10-13 | 1983-10-13 | Hochbromierte polystyrole, verfahren zu deren herstellung und anwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19833337223 DE3337223A1 (de) | 1983-10-13 | 1983-10-13 | Hochbromierte polystyrole, verfahren zu deren herstellung und anwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3337223A1 true DE3337223A1 (de) | 1985-05-02 |
| DE3337223C2 DE3337223C2 (enExample) | 1988-11-10 |
Family
ID=6211715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833337223 Granted DE3337223A1 (de) | 1983-10-13 | 1983-10-13 | Hochbromierte polystyrole, verfahren zu deren herstellung und anwendung |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3337223A1 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4966946A (en) * | 1990-02-02 | 1990-10-30 | Great Lakes Chemical Corporation | Block copolymer of polyalkylene and halogenated polystyrene |
| US5077337A (en) * | 1990-02-22 | 1991-12-31 | Great Lakes Chemical Corporation | Flame retardant graft copolymers of polypropylene |
| EP0528247A1 (en) * | 1991-08-08 | 1993-02-24 | Bromine Compounds Ltd. | Process for the preparation of tribromostyrene and beta bromoethyltribromobenzene |
| US5380802A (en) * | 1992-12-09 | 1995-01-10 | Great Lakes Chemical Corporation | Fire retardant polyolefin fibers and fabrics |
| US7666943B2 (en) | 2004-01-21 | 2010-02-23 | Albemarle Corporation | Flame retarded fibers and filaments and process of production therefor |
| US7666944B2 (en) | 2004-01-21 | 2010-02-23 | Albemarle Corporation | Flame retarded fibers and filaments and process of production therefor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3025666C2 (de) * | 1980-07-07 | 1983-01-20 | Chemische Fabrik Kalk GmbH, 5000 Köln | Polymeres Pentabromstyrol, Verfahren zur Herstellung und Verwendung |
-
1983
- 1983-10-13 DE DE19833337223 patent/DE3337223A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3025666C2 (de) * | 1980-07-07 | 1983-01-20 | Chemische Fabrik Kalk GmbH, 5000 Köln | Polymeres Pentabromstyrol, Verfahren zur Herstellung und Verwendung |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4966946A (en) * | 1990-02-02 | 1990-10-30 | Great Lakes Chemical Corporation | Block copolymer of polyalkylene and halogenated polystyrene |
| USRE35308E (en) * | 1990-02-02 | 1996-07-30 | Shell Oil Company | Block copolymer of polyalkylene and halogenated polystyrene |
| US5077337A (en) * | 1990-02-22 | 1991-12-31 | Great Lakes Chemical Corporation | Flame retardant graft copolymers of polypropylene |
| EP0528247A1 (en) * | 1991-08-08 | 1993-02-24 | Bromine Compounds Ltd. | Process for the preparation of tribromostyrene and beta bromoethyltribromobenzene |
| US5243109A (en) * | 1991-08-08 | 1993-09-07 | Bromine Compounds Ltd. | Tribromostyrene products and process for making them |
| US5380802A (en) * | 1992-12-09 | 1995-01-10 | Great Lakes Chemical Corporation | Fire retardant polyolefin fibers and fabrics |
| US7666943B2 (en) | 2004-01-21 | 2010-02-23 | Albemarle Corporation | Flame retarded fibers and filaments and process of production therefor |
| US7666944B2 (en) | 2004-01-21 | 2010-02-23 | Albemarle Corporation | Flame retarded fibers and filaments and process of production therefor |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3337223C2 (enExample) | 1988-11-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |