GB477843A - The manufacture of new polymerisation products - Google Patents
The manufacture of new polymerisation productsInfo
- Publication number
- GB477843A GB477843A GB1854036A GB1854036A GB477843A GB 477843 A GB477843 A GB 477843A GB 1854036 A GB1854036 A GB 1854036A GB 1854036 A GB1854036 A GB 1854036A GB 477843 A GB477843 A GB 477843A
- Authority
- GB
- United Kingdom
- Prior art keywords
- solvent
- polymerization
- boron fluoride
- epichlorhydrin
- polymerized
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002904 solvent Substances 0.000 abstract 6
- 229910015900 BF3 Inorganic materials 0.000 abstract 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 5
- 238000006116 polymerization reaction Methods 0.000 abstract 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000001816 cooling Methods 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 238000003756 stirring Methods 0.000 abstract 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 239000004902 Softening Agent Substances 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 abstract 1
- SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 abstract 1
- 229940081735 acetylcellulose Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 229920002301 cellulose acetate Polymers 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 210000002741 palatine tonsil Anatomy 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- OCDPVICYFFZSFE-UHFFFAOYSA-N prop-1-enoxybenzene Chemical compound CC=COC1=CC=CC=C1 OCDPVICYFFZSFE-UHFFFAOYSA-N 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 230000000630 rising effect Effects 0.000 abstract 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000002562 thickening agent Substances 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 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
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
-
- 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
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/24—Epihalohydrins
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
Abstract
Oily to resin-like polymerization products are obtained by treating with a small amount of a Friedel-Craft's catalyst a compound of the formula <FORM:0477843/IV/1> in which R and R1 stand for hydrogen or alkyl groups and X stands for a radicle which is free from reactive hydrogen atoms, that is, a radicle which is unable to react with ethylene oxide groups. Thus, X may stand for hydrogen, <FORM:0477843/IV/2> (R2 and R3 being alkyl or aryl). Mixtures of several of the materials above defined, or of these with other reactive oxides, such as ethylene oxide or glycide, may be polymerized. Polymerization may be effected in the presence of an inert solvent, e.g. aliphatic or aromatic hydrocarbons or halogenated aliphatic hydrocarbons. The reaction temperature varies from -25 DEG C. to the boiling point of the starting material or solvent, polymerization being preferably started at low temperature, the temperature being raised towards the end of the reaction. The catalysts are employed in quantities up to 10 per cent. In examples: (1) epichlorhydrin and a small quantity of borofluoride acetic are reacted with stirring and cooling, the temperature rising to 30--50 DEG C. The viscous oil is taken up in a solvent, e.g. carbon tetrachloride and stirred for some hours at 50 DEG C. with caustic soda and tonsil. Insoluble portions are separated and the solvent is distilled off leaving a thick oily polymerizate. Tin tetrachloride or aluminium chloride may be used in place of the borofluoride acetic acid; (2) epichlorhydrin is dissolved in carbon tetrachloride, and a few bubbles of gaseous boron fluoride are passed in while cooling and stirring, whereupon polymerization sets in. After cooling, a few more bubbles of boron fluoride are passed in, and this operation is repeated until the required degree of polymerization is reached. The boron fluoride is removed by treatment with alkaline substances, and the solvent distilled off, a sticky resin being obtained; (3) 1-phenoxypropene oxide-2.3 is polymerized with boron fluoride as in examples 1 and 2, without solvent or dissolved in benzene, chloroform, &c. If no solvent is used, a yellow oil is obtained; (4) a mixture of epichlorhydrin and glycide in any proportion is polymerized as in example 2; (5) 1--3 per cent of boron fluoride is passed into diethylaminoepihydrin and the whole is heated for some hours at 70--90 DEG C. The polymers may be used as softening agents, e.g. for acetyl cellulose, as thickening agents, or as intermediates in the preparation of other compounds; for instance, halogen atoms contained in the molecule may be reacted upon by bases, and the compounds thereby obtained are capable of increasing the affinity of materials for acid wool dyestuffs. Specification 354,992* is referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1854036A GB477843A (en) | 1936-07-03 | 1936-07-03 | The manufacture of new polymerisation products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1854036A GB477843A (en) | 1936-07-03 | 1936-07-03 | The manufacture of new polymerisation products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB477843A true GB477843A (en) | 1938-01-03 |
Family
ID=10114177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1854036A Expired GB477843A (en) | 1936-07-03 | 1936-07-03 | The manufacture of new polymerisation products |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB477843A (en) |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2451185A (en) * | 1946-03-25 | 1948-10-12 | Atherton M Whaley | Fluorinated products and process |
| US2559177A (en) * | 1950-05-01 | 1951-07-03 | Gen Mills Inc | Plasticized polyvinyl resin compositions |
| US2561468A (en) * | 1949-06-16 | 1951-07-24 | J B Williams Company | p-n-mono- and disubstituted aminohydroxyalkylbenzoates and processes of producing same |
| US2599799A (en) * | 1948-02-24 | 1952-06-10 | Gen Mills Inc | Ethers of polymerized epihalohydrin |
| US2871219A (en) * | 1955-04-11 | 1959-01-27 | Dow Chemical Co | Solid polymers of epichlorohydrin |
| US3024219A (en) * | 1959-04-13 | 1962-03-06 | Union Carbide Corp | Polymerization of terminal epoxyalkyl ethers |
| US3058921A (en) * | 1958-03-17 | 1962-10-16 | Shell Oil Co | Epoxy ethers, their preparation and cure |
| US3063948A (en) * | 1959-06-02 | 1962-11-13 | Union Carbide Corp | Copolymers of vicinal-epoxy hydrocarbons with n-2, 3-epoxy carbazoles |
| US3078280A (en) * | 1963-02-19 | Thehx molecule and process of making | ||
| US3106549A (en) * | 1959-08-24 | 1963-10-08 | Hercules Powder Co Ltd | Polymers of lower alkyl glycidates |
| US3112280A (en) * | 1951-08-22 | 1963-11-26 | Ici Ltd | New polymeric substances |
| US3128256A (en) * | 1959-06-02 | 1964-04-07 | Union Carbide Corp | Polymerization of epoxides |
| US3144417A (en) * | 1959-06-02 | 1964-08-11 | Union Carbide Corp | Polymerization of epoxides |
| US3158580A (en) * | 1960-03-11 | 1964-11-24 | Hercules Powder Co Ltd | Poly (epihalohydrin) s |
| US3214390A (en) * | 1960-01-25 | 1965-10-26 | Hercules Powder Co Ltd | Polymeric epoxides |
| US3265656A (en) * | 1963-12-11 | 1966-08-09 | Dow Chemical Co | High acrylonitrile polymer solutions containing polyepihalohydrins |
| US3285862A (en) * | 1964-03-19 | 1966-11-15 | Hercules Inc | Phenyl glycidyl ether-epichlorohydrin copolymer |
| US3288750A (en) * | 1958-07-03 | 1966-11-29 | Gen Tire & Rubber Co | Polymerization of phenyl glycidyl ether |
| US3392145A (en) * | 1959-03-31 | 1968-07-09 | Union Carbide Corp | Polymers of aryl epoxy ethers |
| US3399149A (en) * | 1959-07-01 | 1968-08-27 | Union Carbide Corp | Polymerization of oxirane monoepoxides using an organometallic compound with water as cocatalysts |
| US3403114A (en) * | 1967-02-17 | 1968-09-24 | Hercules Inc | Polymers of amino epoxides |
| US3408404A (en) * | 1963-07-29 | 1968-10-29 | Hercules Inc | Diols of poly(glycidyl ether)s |
| US20120101308A1 (en) * | 2009-06-30 | 2012-04-26 | Basf Se | Method for the phosphine-initialized production of hyperbranched polyols |
-
1936
- 1936-07-03 GB GB1854036A patent/GB477843A/en not_active Expired
Cited By (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3078280A (en) * | 1963-02-19 | Thehx molecule and process of making | ||
| US2451185A (en) * | 1946-03-25 | 1948-10-12 | Atherton M Whaley | Fluorinated products and process |
| US2599799A (en) * | 1948-02-24 | 1952-06-10 | Gen Mills Inc | Ethers of polymerized epihalohydrin |
| US2561468A (en) * | 1949-06-16 | 1951-07-24 | J B Williams Company | p-n-mono- and disubstituted aminohydroxyalkylbenzoates and processes of producing same |
| US2559177A (en) * | 1950-05-01 | 1951-07-03 | Gen Mills Inc | Plasticized polyvinyl resin compositions |
| US3112280A (en) * | 1951-08-22 | 1963-11-26 | Ici Ltd | New polymeric substances |
| US2871219A (en) * | 1955-04-11 | 1959-01-27 | Dow Chemical Co | Solid polymers of epichlorohydrin |
| US3058921A (en) * | 1958-03-17 | 1962-10-16 | Shell Oil Co | Epoxy ethers, their preparation and cure |
| US3288750A (en) * | 1958-07-03 | 1966-11-29 | Gen Tire & Rubber Co | Polymerization of phenyl glycidyl ether |
| US3392145A (en) * | 1959-03-31 | 1968-07-09 | Union Carbide Corp | Polymers of aryl epoxy ethers |
| US3024219A (en) * | 1959-04-13 | 1962-03-06 | Union Carbide Corp | Polymerization of terminal epoxyalkyl ethers |
| US3063948A (en) * | 1959-06-02 | 1962-11-13 | Union Carbide Corp | Copolymers of vicinal-epoxy hydrocarbons with n-2, 3-epoxy carbazoles |
| US3128256A (en) * | 1959-06-02 | 1964-04-07 | Union Carbide Corp | Polymerization of epoxides |
| US3144417A (en) * | 1959-06-02 | 1964-08-11 | Union Carbide Corp | Polymerization of epoxides |
| US3399149A (en) * | 1959-07-01 | 1968-08-27 | Union Carbide Corp | Polymerization of oxirane monoepoxides using an organometallic compound with water as cocatalysts |
| US3106549A (en) * | 1959-08-24 | 1963-10-08 | Hercules Powder Co Ltd | Polymers of lower alkyl glycidates |
| US3214390A (en) * | 1960-01-25 | 1965-10-26 | Hercules Powder Co Ltd | Polymeric epoxides |
| US3158580A (en) * | 1960-03-11 | 1964-11-24 | Hercules Powder Co Ltd | Poly (epihalohydrin) s |
| US3408404A (en) * | 1963-07-29 | 1968-10-29 | Hercules Inc | Diols of poly(glycidyl ether)s |
| US3265656A (en) * | 1963-12-11 | 1966-08-09 | Dow Chemical Co | High acrylonitrile polymer solutions containing polyepihalohydrins |
| US3285862A (en) * | 1964-03-19 | 1966-11-15 | Hercules Inc | Phenyl glycidyl ether-epichlorohydrin copolymer |
| US3403114A (en) * | 1967-02-17 | 1968-09-24 | Hercules Inc | Polymers of amino epoxides |
| US20120101308A1 (en) * | 2009-06-30 | 2012-04-26 | Basf Se | Method for the phosphine-initialized production of hyperbranched polyols |
| US9096713B2 (en) * | 2009-06-30 | 2015-08-04 | Basf Se | Method for the phosphine-initialized production of hyperbranched polyols |
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