GB956698A - New polyepoxides, their preparation and their use - Google Patents
New polyepoxides, their preparation and their useInfo
- Publication number
- GB956698A GB956698A GB4635561A GB4635561A GB956698A GB 956698 A GB956698 A GB 956698A GB 4635561 A GB4635561 A GB 4635561A GB 4635561 A GB4635561 A GB 4635561A GB 956698 A GB956698 A GB 956698A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aliphatic
- formula
- hydrogen
- hydrocarbon residue
- dihydrodicyclopentadiene
- 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
- 229920000647 polyepoxide Polymers 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 5
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- -1 crotyl Chemical group 0.000 abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 2
- 150000001298 alcohols Chemical class 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 150000001735 carboxylic acids Chemical class 0.000 abstract 2
- 238000006735 epoxidation reaction Methods 0.000 abstract 2
- 125000003700 epoxy group Chemical group 0.000 abstract 2
- 239000003822 epoxy resin Substances 0.000 abstract 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- MAAOGZDNJFXJED-UHFFFAOYSA-N C(C1CCCCC1)=C(O)C(O)CO Chemical compound C(C1CCCCC1)=C(O)C(O)CO MAAOGZDNJFXJED-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004593 Epoxy Substances 0.000 abstract 1
- 239000004606 Fillers/Extenders Substances 0.000 abstract 1
- YGSVWQITVDNLMK-UHFFFAOYSA-N OO.C1(CCC(=O)O1)=O Chemical compound OO.C1(CCC(=O)O1)=O YGSVWQITVDNLMK-UHFFFAOYSA-N 0.000 abstract 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 230000000996 additive effect Effects 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 238000006266 etherification reaction Methods 0.000 abstract 1
- 229930195729 fatty acid Natural products 0.000 abstract 1
- 239000000194 fatty acid Substances 0.000 abstract 1
- 150000004665 fatty acids Chemical class 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 125000005644 linolenyl group Chemical group 0.000 abstract 1
- 125000005645 linoleyl group Chemical group 0.000 abstract 1
- 125000005394 methallyl group Chemical group 0.000 abstract 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 150000004965 peroxy acids Chemical class 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/28—Ethers with hydroxy compounds containing oxirane rings
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60B—VEHICLE WHEELS; CASTORS; AXLES FOR WHEELS OR CASTORS; INCREASING WHEEL ADHESION
- B60B11/00—Units comprising multiple wheels arranged side by side; Wheels having more than one rim or capable of carrying more than one tyre
- B60B11/06—Wheels with more than one rim mounted on a single wheel body
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60B—VEHICLE WHEELS; CASTORS; AXLES FOR WHEELS OR CASTORS; INCREASING WHEEL ADHESION
- B60B23/00—Attaching rim to wheel body
- B60B23/06—Attaching rim to wheel body by screws, bolts, pins, or clips
- B60B23/10—Attaching rim to wheel body by screws, bolts, pins, or clips arranged axially
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
Abstract
Polyepoxy compounds of the formula: <FORM:0956698/C2/1> where R1 to R12 are hydrogen or methyl groups and X is an aliphatic or araliphatic hydrocarbon residue substituted by at least one epoxy group are made by epoxidizing a compound of the formula: <FORM:0956698/C2/2> where X1 represents an aliphatic or araliphatic hydrocarbon residue containing at least one carbon to carbon double bond, X1 preferably being a C3 to C22 aliphatic hydrocarbon residue and R1 to 12 all hydrogen, especially when X1 is an allyl residue. Products claimed are restricted to compounds, of formula I wherein X has at least 6 carbon atoms, preferably 6 to 22 carbon atoms. The starting materials may be prepared either by the addition of water to dicyclopentadiene followed by etherification of the alcohol with an alcohol X1-OH, or by the direct formation of the ether by the additive reaction of the alcohol and dicyclopentadiene. Suitable alcohols named are cinnamyl, crotyl, methallyl, rhodinol, oleyl, erucyl, linoleyl, linolenyl and mixtures of unsaturated alcohols produced by hydrogenolysis of unsaturated natural fatty acids. The epoxidation may be effected by the use of peracids, mixtures of carboxylic acids and hydrogen peroxide or the two stage process via the hypohalite may be employed. The examples describe the epoxidation of allyloxy-dihydrodicyclopentadiene using peracetic acid and as alternative succinic anhydride hydrogen peroxide, and oleyloxy-dihydrodicyclopentadiene using peracetic acid. The compounds may be converted to epoxy resins (see Division C3). Specification 950,285 and U.S.A. Specification 2,393,608 are referred to.ALSO:Polyepoxy compounds of the formula: <FORM:0956698/C3/1> where R1 to R12 are hydrogen or methyl and X is an aliphatic or araliphatic hydrocarbon residue substituted by at least one epoxy group, preferably C3 to C22 aliphatic prepared by a novel process (see Division C2) may be condensed with amines, amides, carboxylic acids or their anhydrides, polyols, in the presence of catalysts, together with fillers, diluents and extenders, numerous examples of which are listed, to give epoxy resins. The sole detailed example relates to the condensation of epoxidised allyloxy-dihydrodicyclopentadiene with 3, 4 epoxy hexahydrobenzal glycerol and phthalic anhydride. Specification 950,285 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1465960A CH393297A (en) | 1960-12-30 | 1960-12-30 | Process for the production of new polyepoxy compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB956698A true GB956698A (en) | 1964-04-29 |
Family
ID=4402758
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4635561A Expired GB956698A (en) | 1960-12-30 | 1961-12-27 | New polyepoxides, their preparation and their use |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE612165A (en) |
| CH (1) | CH393297A (en) |
| DE (1) | DE1418748A1 (en) |
| ES (1) | ES273340A1 (en) |
| GB (1) | GB956698A (en) |
| NL (1) | NL273079A (en) |
-
0
- BE BE612165D patent/BE612165A/xx unknown
- NL NL273079D patent/NL273079A/xx unknown
-
1960
- 1960-12-30 CH CH1465960A patent/CH393297A/en unknown
-
1961
- 1961-12-27 GB GB4635561A patent/GB956698A/en not_active Expired
- 1961-12-29 DE DE19611418748 patent/DE1418748A1/en active Pending
- 1961-12-29 ES ES0273340A patent/ES273340A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES273340A1 (en) | 1962-07-01 |
| CH393297A (en) | 1965-06-15 |
| BE612165A (en) | |
| NL273079A (en) | |
| DE1418748A1 (en) | 1968-10-10 |
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