DE2102102A1 - Mischkatalysatoren für die Polymerisation von Epoxid-Verbindungen und Verfahren zur Polymerisation von Epoxid-Verbindungen - Google Patents
Mischkatalysatoren für die Polymerisation von Epoxid-Verbindungen und Verfahren zur Polymerisation von Epoxid-VerbindungenInfo
- Publication number
- DE2102102A1 DE2102102A1 DE19712102102 DE2102102A DE2102102A1 DE 2102102 A1 DE2102102 A1 DE 2102102A1 DE 19712102102 DE19712102102 DE 19712102102 DE 2102102 A DE2102102 A DE 2102102A DE 2102102 A1 DE2102102 A1 DE 2102102A1
- Authority
- DE
- Germany
- Prior art keywords
- epoxy compounds
- polymerization
- compounds
- catalyst
- radical
- 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
- 239000003054 catalyst Substances 0.000 title claims description 42
- 150000001875 compounds Chemical class 0.000 title claims description 16
- 239000004593 Epoxy Substances 0.000 title claims description 14
- 238000006116 polymerization reaction Methods 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 11
- -1 aromatic radical Chemical class 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 8
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 230000027455 binding Effects 0.000 claims 1
- 238000009739 binding Methods 0.000 claims 1
- 230000032683 aging Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 5
- 229910052787 antimony Inorganic materials 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000001463 antimony compounds Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- HXIQYSLFEXIOAV-UHFFFAOYSA-N 2-tert-butyl-4-(5-tert-butyl-4-hydroxy-2-methylphenyl)sulfanyl-5-methylphenol Chemical compound CC1=CC(O)=C(C(C)(C)C)C=C1SC1=CC(C(C)(C)C)=C(O)C=C1C HXIQYSLFEXIOAV-UHFFFAOYSA-N 0.000 description 1
- WMEDSSFYIKNTNG-UHFFFAOYSA-N 3,6-dimethyloctane-3,6-diol Chemical compound CCC(C)(O)CCC(C)(O)CC WMEDSSFYIKNTNG-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- FAPDDOBMIUGHIN-UHFFFAOYSA-K antimony trichloride Chemical compound Cl[Sb](Cl)Cl FAPDDOBMIUGHIN-UHFFFAOYSA-K 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CLRSZXHOSMKUIB-UHFFFAOYSA-M benzenediazonium chloride Chemical compound [Cl-].N#[N+]C1=CC=CC=C1 CLRSZXHOSMKUIB-UHFFFAOYSA-M 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- SXGSCDIYMWXCLC-UHFFFAOYSA-M dibutylstibinic acid Chemical compound CCCC[Sb](O)(=O)CCCC SXGSCDIYMWXCLC-UHFFFAOYSA-M 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- PZICCMKCPLOREP-UHFFFAOYSA-M dimethylstibinic acid Chemical compound C[Sb](C)(O)=O PZICCMKCPLOREP-UHFFFAOYSA-M 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- CIHNSVDTFXXPGZ-UHFFFAOYSA-N oxo(diphenyl)antimony Chemical compound C=1C=CC=CC=1[Sb](=O)C1=CC=CC=C1 CIHNSVDTFXXPGZ-UHFFFAOYSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- KXPRPCQZFKDEGH-UHFFFAOYSA-L phenylstibonic acid Chemical compound O[Sb](O)(=O)C1=CC=CC=C1 KXPRPCQZFKDEGH-UHFFFAOYSA-L 0.000 description 1
- 229920002755 poly(epichlorohydrin) Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- QZRSVBDWRWTHMT-UHFFFAOYSA-M silver;3-carboxy-3,5-dihydroxy-5-oxopentanoate Chemical compound [Ag+].OC(=O)CC(O)(C([O-])=O)CC(O)=O QZRSVBDWRWTHMT-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- ORYGRKHDLWYTKX-UHFFFAOYSA-N trihexylalumane Chemical compound CCCCCC[Al](CCCCCC)CCCCCC ORYGRKHDLWYTKX-UHFFFAOYSA-N 0.000 description 1
- QNEHTJFWGHSTEF-UHFFFAOYSA-N triphenylstibane;dihydrate Chemical compound O.O.C1=CC=CC=C1[Sb](C=1C=CC=CC=1)C1=CC=CC=C1 QNEHTJFWGHSTEF-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/12—Saturated oxiranes characterised by the catalysts used containing organo-metallic compounds or metal hydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712102102 DE2102102A1 (de) | 1971-01-18 | 1971-01-18 | Mischkatalysatoren für die Polymerisation von Epoxid-Verbindungen und Verfahren zur Polymerisation von Epoxid-Verbindungen |
| IT32091/71A IT943751B (it) | 1971-01-18 | 1971-12-06 | Catalizzatori misti per la polime rizzazione di composti epossidici e procedimento per polimerizzare tali composti |
| US00213823A US3767599A (en) | 1971-01-18 | 1971-12-29 | Mixed metallo organic catalysts for the polymerization of epoxy compounds and methods for the polymerization of epoxy compounds using saidcatalysts |
| NL7200714A NL7200714A (enExample) | 1971-01-18 | 1972-01-18 | |
| BE778187A BE778187A (fr) | 1971-01-18 | 1972-01-18 | Polymerisation d'epoxydes |
| FR7201540A FR2122487B1 (enExample) | 1971-01-18 | 1972-01-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712102102 DE2102102A1 (de) | 1971-01-18 | 1971-01-18 | Mischkatalysatoren für die Polymerisation von Epoxid-Verbindungen und Verfahren zur Polymerisation von Epoxid-Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2102102A1 true DE2102102A1 (de) | 1972-09-07 |
Family
ID=5796164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712102102 Pending DE2102102A1 (de) | 1971-01-18 | 1971-01-18 | Mischkatalysatoren für die Polymerisation von Epoxid-Verbindungen und Verfahren zur Polymerisation von Epoxid-Verbindungen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3767599A (enExample) |
| BE (1) | BE778187A (enExample) |
| DE (1) | DE2102102A1 (enExample) |
| FR (1) | FR2122487B1 (enExample) |
| IT (1) | IT943751B (enExample) |
| NL (1) | NL7200714A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650853A (en) * | 1985-11-15 | 1987-03-17 | The Dow Chemical Company | Process of polymerizing epoxides in solvent mixtures to form granular polymer products |
-
1971
- 1971-01-18 DE DE19712102102 patent/DE2102102A1/de active Pending
- 1971-12-06 IT IT32091/71A patent/IT943751B/it active
- 1971-12-29 US US00213823A patent/US3767599A/en not_active Expired - Lifetime
-
1972
- 1972-01-18 BE BE778187A patent/BE778187A/xx unknown
- 1972-01-18 FR FR7201540A patent/FR2122487B1/fr not_active Expired
- 1972-01-18 NL NL7200714A patent/NL7200714A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2122487A1 (enExample) | 1972-09-01 |
| NL7200714A (enExample) | 1972-07-20 |
| FR2122487B1 (enExample) | 1975-02-07 |
| US3767599A (en) | 1973-10-23 |
| BE778187A (fr) | 1972-07-18 |
| IT943751B (it) | 1973-04-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHA | Expiration of time for request for examination |