GB867461A - Process for the production of organic compounds of high molecular weight from an organic compound contanining at least one linear or cyclic acetal group, an alkylene oxide and a compound containing at least one reactive carbon-to-carbon double bond - Google Patents
Process for the production of organic compounds of high molecular weight from an organic compound contanining at least one linear or cyclic acetal group, an alkylene oxide and a compound containing at least one reactive carbon-to-carbon double bondInfo
- Publication number
- GB867461A GB867461A GB11432/59A GB1143259A GB867461A GB 867461 A GB867461 A GB 867461A GB 11432/59 A GB11432/59 A GB 11432/59A GB 1143259 A GB1143259 A GB 1143259A GB 867461 A GB867461 A GB 867461A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacted
- polyacetal
- styrene
- propylene oxide
- boron trifluoride
- 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
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
- C08G4/00—Condensation polymers of aldehydes or ketones with polyalcohols; Addition polymers of heterocyclic oxygen compounds containing in the ring at least once the grouping —O—C—O—
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- 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/06—Catalysts
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- 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
- C08G2/00—Addition polymers of aldehydes or cyclic oligomers thereof or of ketones; Addition copolymers thereof with less than 50 molar percent of other substances
- C08G2/18—Copolymerisation of aldehydes or ketones
- C08G2/24—Copolymerisation of aldehydes or ketones with acetals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
High molecular weight organic compounds are prepared by reacting a compound containing at least one linear or cyclic acetal group with an alkylene oxide and with a compound containing at least one carbon-to-carbon double bond in the presence of a catalyst. Suitable acetal compounds are reaction products of formaldehyde, acetaldehyde, benzaldehyde or glyoxal with hydroxy compounds, e.g. methanol, ethanol, b -chloroethanol, propanol, benzyl alcohol, propyl alcohol, cyclohexanol, allyl or oleyl alcohol, pentanediols, hexanediols, 7, 18, -dihydroxyoctadecane, 2-butane-1, 4-diol, 2-butyne-1, 4-diol, trimethylol propane, glycerine, sorbitol, 4, 41-dihydroxy dycyclohexyl methane, ethylene glycol, propane-1, 2- or 1, 3-diol, butane or butene-diols, condensates of alkylene oxides with such alcohols or phenols, glycerine monomethyl methacrylate, trimethylol propane monoallyl ether, castor oil, phthalic acid diglycol ester, hydroxyl-containing polyesters, polythioethers with terminal OH groups, polyvinyl alcohol, and adipic acid-bishydroxyethyl methylamide. Other suitable polyacetals can be prepared from condensates of formaldehyde with xylene, phenols, urea or melamine. Suitable alkylene oxides are ethylene, trimethylene, propylene, butylene or styrene oxide, oxides as described in Specification 758,450, epichlorhydrin, 3-ethyl-3-hydroxymethyl trimethylene oxide, 1-allyl-hydroxy-2, 3-epoxypropane, reaction products of unsaturated carboxylic acids with peroxidic compounds, vinyl cyclohene oxide, dioxaspiroheptane, butadiene dioxide, and glycidyl ethers obtained by reacting epichlorhydrin with a polyhydric compound. Some olefins mentioned are ethylene, propylene, butylene, styrene, butadiene, isoprene, divinyl benzene, cyclopentadiene, vinyl chloride, allyl chloride, acrylonitrile, maleic or cinnamic acid esters, and chloroprene. Suitable catalysts are boron trihalides and their ether adducts, acid chlorides of chlorosulphonic acid type, ferric chloride, AlCl, SbCl3 and others usual for ionic polymerization. Reaction may be in solvents, e.g. hydrocarbons, chlorinated hydrocarbons, esters, ethers, ketones. Polymerization inhibitors, e.g. hydroquinone may also be present. In Examples (1) trimethylene glycolformaldehyde polyacetal and propylene oxide are reacted in presence of boron trifluoride diethyl ether etherate and the product reacted with styrene; (2) Styrene and propylene oxide are reacted with a mixture of dimethyl formal, boron trifluoride diethyl ether etherate and hydroquinone; (3) is similar to (2) but uses a polyacetal from trioxyethylated trimethylol propane and formaldehyde; (4) Butane-1, 4-diol methylene ether is treated with boron trifluoride and the viscous product, after addition of hydroquinone is reacted with propylene oxide and chloroprene; (5) A styrene-propylene oxide mixture is reacted with 4-phenyl-1, 3-dioxane in presence of hydroquinone and boron trifluoride diethyl ether etherate; (6) Boron trifluoride-tetrahydrofuran etherate, hydroquinone, and butane-1, 4-dioxethyl glycol formaldehyde polyacetal were mixed, and butadiene and propylene oxide were added dropwise to react; (7) is similar to (3) with epichlorhydrin replacing the propylene oxide; (8) Boron trifluoride-tetrahydrofuran etherate is mixed with the polyacetal of Example 1, and the mixture reacted with styrene, propylene oxide and a polyglycidyl ether from butane diol and epichlorhydrin; (9) Diethylene glycolformaldehyde polyacetal, hydroquinone and boron trifluoride-tetrahydrofuran etherate are reacted with 3-ethyl-3-hydroxymethyl trimethylene oxide and styrene; (10) The polyacetal of Example 6, hydroquinone and FeCl3 are reacted with propylene oxide and styrene; (11) Boron trifluoride is mixed with the polyacetal of Example 1 and 1-allyloxy-2, 3-epoxypropane; (12) The polyacetal of Example 1 is reacted with ethylene oxide in presence of boron trifluoride-tetrahydrofuran etherate and the product reacted with styrene; (13) The polyacetal of Example 1 is mixed with boron trifluoride-di-ethyl ether etherate and hydroquinone. The mixture is reacted with isobutylene and propylene oxide; (14) The polyacetal of Example 1 is used with AlCl3, hydroquinone, styrene and styrene oxide; (15) The polyacetal of Example 6 is reacted with propylene oxide in presence of FeCl3 and the product reacted with propylene oxide and isobutylene. By choosing reactants to give products with reactive groups, e.g. hydroxyl, terminal halogen or double bonds the products may be subjected to further reactions, e.g. for modifying polyesters or epoxide resins or for making plastics by the polyisocyanate polyaddition process. The products also find uses as plasticisers or emulsifiers.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE867461X | 1958-04-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB867461A true GB867461A (en) | 1961-05-10 |
Family
ID=6802143
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB11432/59A Expired GB867461A (en) | 1958-04-03 | 1959-04-03 | Process for the production of organic compounds of high molecular weight from an organic compound contanining at least one linear or cyclic acetal group, an alkylene oxide and a compound containing at least one reactive carbon-to-carbon double bond |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB867461A (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4581470A (en) * | 1983-09-27 | 1986-04-08 | Union Carbide Corporation | Novel polyols and uses thereof |
US4594366A (en) * | 1983-06-29 | 1986-06-10 | Union Carbide Corporation | Connected branched polyols and polyurethanes based thereon |
US4659772A (en) * | 1983-09-27 | 1987-04-21 | Union Carbide Corporation | Novel polymer/polyols and uses thereof |
US4727094A (en) * | 1983-09-27 | 1988-02-23 | Union Carbide Corporation | Method for producing polyurethanes |
-
1959
- 1959-04-03 GB GB11432/59A patent/GB867461A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4594366A (en) * | 1983-06-29 | 1986-06-10 | Union Carbide Corporation | Connected branched polyols and polyurethanes based thereon |
US4581470A (en) * | 1983-09-27 | 1986-04-08 | Union Carbide Corporation | Novel polyols and uses thereof |
US4659772A (en) * | 1983-09-27 | 1987-04-21 | Union Carbide Corporation | Novel polymer/polyols and uses thereof |
US4727094A (en) * | 1983-09-27 | 1988-02-23 | Union Carbide Corporation | Method for producing polyurethanes |
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