DE2622134A1 - Phosphoryliertes polystyrol und verfahren zu dessen herstellung - Google Patents
Phosphoryliertes polystyrol und verfahren zu dessen herstellungInfo
- Publication number
- DE2622134A1 DE2622134A1 DE19762622134 DE2622134A DE2622134A1 DE 2622134 A1 DE2622134 A1 DE 2622134A1 DE 19762622134 DE19762622134 DE 19762622134 DE 2622134 A DE2622134 A DE 2622134A DE 2622134 A1 DE2622134 A1 DE 2622134A1
- Authority
- DE
- Germany
- Prior art keywords
- copolymer
- amide
- catalyst
- polystyrene
- hydroxymethyl
- 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.)
- Withdrawn
Links
- 239000004793 Polystyrene Substances 0.000 title claims description 31
- 229920002223 polystyrene Polymers 0.000 title claims description 31
- 238000000034 method Methods 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000003054 catalyst Substances 0.000 claims description 30
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 23
- 150000001408 amides Chemical class 0.000 claims description 21
- 229920001577 copolymer Polymers 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 14
- 229910052698 phosphorus Inorganic materials 0.000 claims description 14
- 239000011574 phosphorus Substances 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical class [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 8
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- 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 claims description 2
- 125000005997 bromomethyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000002743 phosphorus functional group Chemical group 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- JQZSKHZKLNKYQS-UHFFFAOYSA-N OP(O)=O.OP(O)=O.OP(O)=O.P.P Chemical compound OP(O)=O.OP(O)=O.OP(O)=O.P.P JQZSKHZKLNKYQS-UHFFFAOYSA-N 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 description 15
- 238000006467 substitution reaction Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 6
- 230000026731 phosphorylation Effects 0.000 description 5
- 238000006366 phosphorylation reaction Methods 0.000 description 5
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl radical Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- 229940080818 propionamide Drugs 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- IDMCOIZLZMSKJZ-UHFFFAOYSA-N 2-diethoxyphosphoryl-n-(hydroxymethyl)acetamide Chemical compound CCOP(=O)(OCC)CC(=O)NCO IDMCOIZLZMSKJZ-UHFFFAOYSA-N 0.000 description 1
- QPVCUQOSWAXEOQ-UHFFFAOYSA-N 2-diethoxyphosphorylacetamide Chemical compound CCOP(=O)(CC(N)=O)OCC QPVCUQOSWAXEOQ-UHFFFAOYSA-N 0.000 description 1
- 206010006784 Burning sensation Diseases 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009970 fire resistant effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- C08F8/40—Introducing phosphorus atoms or phosphorus-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/579,435 US4007318A (en) | 1975-05-21 | 1975-05-21 | Phosphorylated polystyrene and method for forming same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2622134A1 true DE2622134A1 (de) | 1976-12-02 |
Family
ID=24316891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762622134 Withdrawn DE2622134A1 (de) | 1975-05-21 | 1976-05-19 | Phosphoryliertes polystyrol und verfahren zu dessen herstellung |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4007318A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS51140991A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2622134A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2311788A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1552798A (cg-RX-API-DMAC7.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8003059A (nl) * | 1980-05-28 | 1982-01-04 | Stamicarbon | Werkwijze en katalysator voor het uitvoeren van hydroformyleringsreacties. |
| US4581415A (en) * | 1983-11-03 | 1986-04-08 | Allied Corporation | Polymer-bound alkyl diarylphosphinite catalyst compositions and processes for making same |
| US4710545A (en) * | 1984-07-31 | 1987-12-01 | Allied Corporation | Polymer-bound alkyl diarylphosphinite catalyst compositions and processes for making same |
| DE3711092A1 (de) * | 1987-04-02 | 1988-10-13 | Pfersee Chem Fab | Verfahren zur herstellung eines wasserloeslichen, selbsthaertenden, polymeren kondensationsproduktes, dessen waessrige loesungen und verwendung |
| JP2007525563A (ja) * | 2004-02-27 | 2007-09-06 | 株式会社荏原製作所 | ホスホリル基を有する共重合体およびその成形品 |
| CN103422772B (zh) * | 2012-05-24 | 2015-04-08 | 中国林业科学研究院木材工业研究所 | 一种木塑复合材料型材及其制备方法 |
| CN104405075B (zh) * | 2014-11-11 | 2016-07-06 | 南京工业职业技术学院 | 一种复合墙体板材及其制备方法 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2569400A (en) * | 1948-05-27 | 1951-09-25 | Monsanto Chemicals | Alkylation of polystyrene using a hydrogen fluoride catalyst |
| US2911378A (en) * | 1952-01-02 | 1959-11-03 | Nat Aluminate Corp | Water insoluble phosphonic acid polymerizates of polyvinylaryl compounds |
| US3051740A (en) * | 1960-01-04 | 1962-08-28 | Monsanto Chemicals | Ethylenically unsaturated aromatic phosphorus acids |
| BE647376A (cg-RX-API-DMAC7.html) * | 1963-05-03 | |||
| CH445126A (de) * | 1963-09-18 | 1967-10-15 | Ciba Geigy | Verfahren zur Herstellung Phosphor enthaltender Polymerisate |
| US3423369A (en) * | 1966-01-14 | 1969-01-21 | Ciba Ltd | Phosphorus-containing aminoplasts and process for their preparation |
| CH473937A (de) * | 1966-06-01 | 1969-07-31 | Ciba Geigy | Verfahren zum Flammfestmachen von cellulosehaltigen Textilmaterialien |
| CH475408A (de) * | 1967-04-11 | 1969-08-29 | Ciba Geigy | Verwendung von Phosphorverbindungen zum Flammfestmachen von cellulosehaltigem textilem Fasermaterial |
| DE1618408A1 (de) * | 1967-04-25 | 1970-12-17 | Bayer Ag | Verfahren zur Herstellung von Additionsprodukten aus Estern und oder Amiden von Saeuren des Phosphors und organischen Isocyanaten |
| CH552021A (de) * | 1970-02-06 | 1974-07-31 | Ciba Geigy Ag | Verfahren zur herstellung und verwendung von phosphonocarbonsaeureamiden ausserhalb der textilindustrie. |
| CH524008A (de) * | 1970-04-27 | 1971-12-15 | Ciba Geigy Ag | Verfahren zum Flammfestmachen von Textilmaterialien aus Polyester und Cellulose |
| US3742095A (en) * | 1970-07-13 | 1973-06-26 | Stauffer Chemical Co | Hydroxyalkylcarbamylalkylphosphonates |
| US3865796A (en) * | 1970-10-27 | 1975-02-11 | Hoechst Ag | Phosphorus-containing polymers |
| DE2114610A1 (de) * | 1971-03-26 | 1972-10-05 | Badische Anilin- & Soda-Fabrik Ag, 6700 Ludwigshafen | Derivate mehrwertiger Alkohole |
| US3816068A (en) * | 1971-07-12 | 1974-06-11 | Burlington Industries Inc | Flame retardant for cellulosic fabrics |
| JPS49109700A (cg-RX-API-DMAC7.html) * | 1973-02-28 | 1974-10-18 | ||
| US3903337A (en) * | 1974-04-04 | 1975-09-02 | Mitsui Toatsu Chemicals | Method for processing cellulose containing material to impart flame resistance |
-
1975
- 1975-05-21 US US05/579,435 patent/US4007318A/en not_active Expired - Lifetime
-
1976
- 1976-05-18 JP JP51056164A patent/JPS51140991A/ja active Pending
- 1976-05-18 GB GB20473/76A patent/GB1552798A/en not_active Expired
- 1976-05-19 DE DE19762622134 patent/DE2622134A1/de not_active Withdrawn
- 1976-05-21 FR FR7615326A patent/FR2311788A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS51140991A (en) | 1976-12-04 |
| FR2311788A1 (fr) | 1976-12-17 |
| GB1552798A (en) | 1979-09-19 |
| US4007318A (en) | 1977-02-08 |
| FR2311788B1 (cg-RX-API-DMAC7.html) | 1980-09-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |