DE2457233A1 - Verfahren zur herstellung von polyalkylenoxiden mit urethanendgruppen - Google Patents
Verfahren zur herstellung von polyalkylenoxiden mit urethanendgruppenInfo
- Publication number
- DE2457233A1 DE2457233A1 DE19742457233 DE2457233A DE2457233A1 DE 2457233 A1 DE2457233 A1 DE 2457233A1 DE 19742457233 DE19742457233 DE 19742457233 DE 2457233 A DE2457233 A DE 2457233A DE 2457233 A1 DE2457233 A1 DE 2457233A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- polyalkylene oxides
- group
- acid chloride
- polyalkylene oxide
- 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
- 229920000233 poly(alkylene oxides) Polymers 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 13
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000000370 acceptor Substances 0.000 claims description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- -1 chlorocarbonic acid ester Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 235000011121 sodium hydroxide Nutrition 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 3
- 235000002639 sodium chloride Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 150000003672 ureas Chemical class 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
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33344—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing carbamate group
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742457233 DE2457233A1 (de) | 1974-12-04 | 1974-12-04 | Verfahren zur herstellung von polyalkylenoxiden mit urethanendgruppen |
| GB4491775A GB1512800A (en) | 1974-12-04 | 1975-10-30 | Process for the production of polyalkylene oxides with terminal urethane groups |
| LU73915A LU73915A1 (en, 2012) | 1974-12-04 | 1975-12-02 | |
| DD18981875A DD124387A5 (en, 2012) | 1974-12-04 | 1975-12-02 | |
| NL7514025A NL7514025A (nl) | 1974-12-04 | 1975-12-02 | Werkwijze voor de bereiding van polyalkyleenoxy- den met eindstandige urethangroepen. |
| BE162395A BE836217A (fr) | 1974-12-04 | 1975-12-03 | Procede pour la preparation d' oxydes de polyalkylene a groupes ubethanne terminaux |
| IE263475A IE42197B1 (en) | 1974-12-04 | 1975-12-03 | Process for the production of polyalkylene oxides with terminal urethane groups |
| ES443170A ES443170A1 (es) | 1974-12-04 | 1975-12-03 | Procedimiento para la obtencion de oxidos polialquilenicos con grupos finales uretano. |
| DK545675A DK545675A (da) | 1974-12-04 | 1975-12-03 | Fremgangsmade til fremstilling af polyalkylenoxider med urethanendegrupper |
| JP14302575A JPS5182396A (ja) | 1974-12-04 | 1975-12-03 | Matsutanuretankiojusuruhoriarukirenokishidono seizohoho |
| FR7537188A FR2293451A1 (fr) | 1974-12-04 | 1975-12-04 | Procede pour la preparation d'oxydes de polyalkylene a groupes urethanne terminaux |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742457233 DE2457233A1 (de) | 1974-12-04 | 1974-12-04 | Verfahren zur herstellung von polyalkylenoxiden mit urethanendgruppen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2457233A1 true DE2457233A1 (de) | 1976-06-10 |
Family
ID=5932434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742457233 Pending DE2457233A1 (de) | 1974-12-04 | 1974-12-04 | Verfahren zur herstellung von polyalkylenoxiden mit urethanendgruppen |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5182396A (en, 2012) |
| BE (1) | BE836217A (en, 2012) |
| DD (1) | DD124387A5 (en, 2012) |
| DE (1) | DE2457233A1 (en, 2012) |
| DK (1) | DK545675A (en, 2012) |
| ES (1) | ES443170A1 (en, 2012) |
| FR (1) | FR2293451A1 (en, 2012) |
| GB (1) | GB1512800A (en, 2012) |
| IE (1) | IE42197B1 (en, 2012) |
| LU (1) | LU73915A1 (en, 2012) |
| NL (1) | NL7514025A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197409A (en) * | 1978-08-08 | 1980-04-08 | Chevron Research Company | Poly(oxyalkylene)aminocarbomates of alkylene polyamine |
| US4329240A (en) | 1979-07-02 | 1982-05-11 | Chevron Research Company | Lubricating oil compositions containing dispersant additives |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4111920A (en) * | 1975-04-30 | 1978-09-05 | Bayer Aktiengesellschaft | Polyether urethanes as antistatic additives in polyamide compositions |
| EP0295031A3 (en) * | 1987-06-12 | 1991-05-08 | SMITH & NEPHEW plc | Orthopaedic splinting material |
| DE4114097C2 (de) * | 1991-04-30 | 1994-03-10 | Thiemt Ohg Geb | Vorrichtung zur Pulverbeschichtung |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3652258A (en) * | 1969-10-27 | 1972-03-28 | Llewellyn W Francher | Method of controlling weeds with phenoxyethyl carbamates |
| DE2409715C3 (de) * | 1974-03-01 | 1979-10-04 | Bayer Ag, 5090 Leverkusen | Antistatische Polyamidmassen, ihre Verwendung und Verfahren zu ihrer Herstellung |
-
1974
- 1974-12-04 DE DE19742457233 patent/DE2457233A1/de active Pending
-
1975
- 1975-10-30 GB GB4491775A patent/GB1512800A/en not_active Expired
- 1975-12-02 DD DD18981875A patent/DD124387A5/xx unknown
- 1975-12-02 NL NL7514025A patent/NL7514025A/xx not_active Application Discontinuation
- 1975-12-02 LU LU73915A patent/LU73915A1/xx unknown
- 1975-12-03 ES ES443170A patent/ES443170A1/es not_active Expired
- 1975-12-03 IE IE263475A patent/IE42197B1/en unknown
- 1975-12-03 DK DK545675A patent/DK545675A/da unknown
- 1975-12-03 JP JP14302575A patent/JPS5182396A/ja active Pending
- 1975-12-03 BE BE162395A patent/BE836217A/xx unknown
- 1975-12-04 FR FR7537188A patent/FR2293451A1/fr not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4197409A (en) * | 1978-08-08 | 1980-04-08 | Chevron Research Company | Poly(oxyalkylene)aminocarbomates of alkylene polyamine |
| US4329240A (en) | 1979-07-02 | 1982-05-11 | Chevron Research Company | Lubricating oil compositions containing dispersant additives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2293451A1 (fr) | 1976-07-02 |
| NL7514025A (nl) | 1976-06-09 |
| BE836217A (fr) | 1976-06-03 |
| GB1512800A (en) | 1978-06-01 |
| LU73915A1 (en, 2012) | 1976-11-11 |
| JPS5182396A (ja) | 1976-07-19 |
| IE42197B1 (en) | 1980-06-18 |
| DD124387A5 (en, 2012) | 1977-02-16 |
| IE42197L (en) | 1976-06-04 |
| ES443170A1 (es) | 1977-04-16 |
| DK545675A (da) | 1976-06-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |