DE1066742B - Verfahren zur Herstellung hochmolekularer Polymerisate und Mischpolymerisate von a-Merhylstyrol und am Kern substituierten Derivaten des a-Methylstyrols - Google Patents
Verfahren zur Herstellung hochmolekularer Polymerisate und Mischpolymerisate von a-Merhylstyrol und am Kern substituierten Derivaten des a-MethylstyrolsInfo
- Publication number
- DE1066742B DE1066742B DENDAT1066742D DE1066742DA DE1066742B DE 1066742 B DE1066742 B DE 1066742B DE NDAT1066742 D DENDAT1066742 D DE NDAT1066742D DE 1066742D A DE1066742D A DE 1066742DA DE 1066742 B DE1066742 B DE 1066742B
- Authority
- DE
- Germany
- Prior art keywords
- methylstyrene
- derivatives
- parts
- polymerization
- molecular weight
- 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.)
- Pending
Links
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical group CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 13
- 229920006158 high molecular weight polymer Polymers 0.000 title claims description 4
- 229920001577 copolymer Polymers 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 239000011541 reaction mixture Substances 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 229920000578 graft copolymer Polymers 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 6
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 4
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- -1 For example Chemical class 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000005662 Paraffin oil Substances 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OINMNNGQSFIOQI-UHFFFAOYSA-N 1-butyl-4-prop-1-en-2-ylbenzene Chemical compound CCCCC1=CC=C(C(C)=C)C=C1 OINMNNGQSFIOQI-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- QDMRQDKMCNPQQH-UHFFFAOYSA-N boranylidynetitanium Chemical compound [B].[Ti] QDMRQDKMCNPQQH-UHFFFAOYSA-N 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 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
- 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
- C08F12/12—Monomers containing a branched unsaturated aliphatic radical or a ring substituted by an alkyl radical
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE850909X | 1958-04-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1066742B true DE1066742B (de) | 1959-10-08 |
Family
ID=6779232
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1065611D Pending DE1065611B (de) | 1958-04-16 | Verfahren zur Herstellung von hochmolekularen Polymerisaten und Mischpolymerisaten von a-Methylstyrol und dessen am Kern substituierten Derivaten | |
| DENDAT1066742D Pending DE1066742B (de) | 1958-04-16 | Verfahren zur Herstellung hochmolekularer Polymerisate und Mischpolymerisate von a-Merhylstyrol und am Kern substituierten Derivaten des a-Methylstyrols |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1065611D Pending DE1065611B (de) | 1958-04-16 | Verfahren zur Herstellung von hochmolekularen Polymerisaten und Mischpolymerisaten von a-Methylstyrol und dessen am Kern substituierten Derivaten |
Country Status (4)
| Country | Link |
|---|---|
| DE (2) | DE1066742B (enrdf_load_stackoverflow) |
| FR (1) | FR1219985A (enrdf_load_stackoverflow) |
| GB (1) | GB850909A (enrdf_load_stackoverflow) |
| NL (1) | NL238180A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1138938B (de) * | 1959-12-14 | 1962-10-31 | Huels Chemische Werke Ag | Verfahren zur Herstellung von waermefesten Mischpolymerisaten aus Styrol und in ª‡-Stellung alkylierten Styrolen |
| DE1189717B (de) | 1963-05-08 | 1965-03-25 | Ruetgerswerke Und Teerverwertu | Verfahren zur Herstellung von hochmolekularen Polymerisaten und Mischpolymerisaten von alpha-Methylstyrol |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1270579B (de) * | 1962-11-24 | 1968-06-20 | Basf Ag | Verfahren zur Herstellung langsam wirkender Duengemittel |
| NL302245A (enrdf_load_stackoverflow) * | 1963-01-18 | |||
| DD237754A3 (de) * | 1982-07-23 | 1986-07-30 | Buna Chem Werke Veb | Verfahren zur oligomerisierung von vinylaromaten mit alkalimetallinitiatoren |
| FR2852960B1 (fr) | 2003-03-31 | 2006-06-23 | Commissariat Energie Atomique | Procede de preparation de poly(alpha-methylstyrene); |
-
0
- NL NL238180D patent/NL238180A/xx unknown
- DE DENDAT1065611D patent/DE1065611B/de active Pending
- DE DENDAT1066742D patent/DE1066742B/de active Pending
-
1959
- 1959-04-15 GB GB12746/59A patent/GB850909A/en not_active Expired
- 1959-04-16 FR FR792243A patent/FR1219985A/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1138938B (de) * | 1959-12-14 | 1962-10-31 | Huels Chemische Werke Ag | Verfahren zur Herstellung von waermefesten Mischpolymerisaten aus Styrol und in ª‡-Stellung alkylierten Styrolen |
| DE1189717B (de) | 1963-05-08 | 1965-03-25 | Ruetgerswerke Und Teerverwertu | Verfahren zur Herstellung von hochmolekularen Polymerisaten und Mischpolymerisaten von alpha-Methylstyrol |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1219985A (fr) | 1960-05-20 |
| GB850909A (en) | 1960-10-12 |
| DE1065611B (de) | 1959-09-17 |
| NL238180A (enrdf_load_stackoverflow) |
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