GB967351A - Improvements in and relating to the preparation of boron trifluoride-oxime complexes and the use of such complexes as hardeners for synthetic resins - Google Patents
Improvements in and relating to the preparation of boron trifluoride-oxime complexes and the use of such complexes as hardeners for synthetic resinsInfo
- Publication number
- GB967351A GB967351A GB18804/62A GB1880462A GB967351A GB 967351 A GB967351 A GB 967351A GB 18804/62 A GB18804/62 A GB 18804/62A GB 1880462 A GB1880462 A GB 1880462A GB 967351 A GB967351 A GB 967351A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oxime
- ether
- complexes
- boron trifluoride
- cycloaliphatic
- 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
- 239000004848 polyfunctional curative Substances 0.000 title abstract 5
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title abstract 3
- 229910052796 boron Inorganic materials 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 2
- 239000000057 synthetic resin Substances 0.000 title 1
- 229920003002 synthetic resin Polymers 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 abstract 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 8
- -1 cycloaliphatic Chemical group 0.000 abstract 8
- 229920000647 polyepoxide Polymers 0.000 abstract 6
- 239000003822 epoxy resin Substances 0.000 abstract 5
- 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 5
- 239000002904 solvent Substances 0.000 abstract 5
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 239000000243 solution Substances 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 150000002923 oximes Chemical class 0.000 abstract 3
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- 239000004952 Polyamide Substances 0.000 abstract 2
- 239000004721 Polyphenylene oxide Substances 0.000 abstract 2
- 125000001931 aliphatic group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 150000001733 carboxylic acid esters Chemical class 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 150000004985 diamines Chemical class 0.000 abstract 2
- 150000001993 dienes Chemical class 0.000 abstract 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 2
- 238000010790 dilution Methods 0.000 abstract 2
- 239000012895 dilution Substances 0.000 abstract 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229920002647 polyamide Polymers 0.000 abstract 2
- 229920000570 polyether Polymers 0.000 abstract 2
- 239000001294 propane Substances 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000004982 aromatic amines Chemical class 0.000 abstract 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 238000005266 casting Methods 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000001816 cooling Methods 0.000 abstract 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 abstract 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 abstract 1
- 239000010439 graphite Substances 0.000 abstract 1
- 229910002804 graphite Inorganic materials 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 238000010030 laminating Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 239000000049 pigment Substances 0.000 abstract 1
- 229920000768 polyamine Polymers 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 239000011253 protective coating Substances 0.000 abstract 1
- 239000010453 quartz Substances 0.000 abstract 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007787 solid Substances 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
- 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
- C08G59/68—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 catalysts used
- C08G59/72—Complexes of boron halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
-
- 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
- C08G59/40—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 curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/405—Oximes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Epoxy Compounds (AREA)
Abstract
Boron trifluoride-oxime complexes are made by dissolving an oxime or ether thereof of the formula R1.C(R2)=N-OR3 where each of R1 and R2 is a monovalent aliphatic, cycloaliphatic, aromatic, araliphatic or heterocyclic radical, or a hydrogen atom and R1 and R2 are the same or different, or where R1.C(R2)= is a divalent cycloaliphatic or heterocyclic radical, and where R3 is a hydrogen atom or a monovalent organic radical, in boron trifluoride diethyl etherate, if necessary at an elevated temperature, and removing the solvent therefrom, if necessary after cooling the solution. The oxime or ether may be derived from acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, benzophenone, cyclohexanone, furfural, acetaldehyde and benzaldehyde. Detailed examples are given. The complexes are used as hardeners for epoxy resins. Solutions of the BF3-oxime complexes in an alcohol or a mono or polyether containing at least one free hydroxyl group or in a mixture of two or more of said solvents are preferred.ALSO:Epoxy resins are hardened using a boron trifluoride-oxime complex derived from an oxime or ether thereof of the formula R1-C(R2)=N-OR3 where each of R1 and R2 is a monovalent aliphatic, cycloaliphatic, aromatic, araliphatic or heterocyclic radical, or a hydrogen atom, and R1 and R2 are the same or different, or where R1-C(R2)=is a divalent cycloaliphatic or heterocyclic radical, and R3 is a hydrogen atom or a monovalent organic radical, by reaction with a boron trifluoride diethyl etherate. The BF3-oxime complexes may be used in solution in an alcohol or a mono- or poly-ether containing at least one free hydroxyl group, or mixtures of two or more of these solvents. Conventional amine hardeners such as alkylol-amine, diamine, triamine, polyamine or polyamide may be used as accelerators. Suitable epoxy resins are diglycidyl and polyglycidyl esters, epoxidized diolefins, dienes or cyclic dienes, diolefin-unsaturated carboxylic esters and carboxylic esters containing two cyclohexenyl radicals, glycidyl polyethers of divalent or polyvalent alcohols or phenols or basic polyepoxides derived from aromatic amines and epichlorhydrin. Particularly suitable are epoxy resins made from bis(4-oxyphenyl) 2,2-propane. Mixtures of liquid or solid epoxy resins in solution with the BF3-oxime hardeners may be used for the preparation of casting resins, protective coatings, laminating resins and adhesives. They may contain fillers such as powdered quartz, ground shale, chalk, alumina minerals, graphite, and also pigments, softeners or solvents. In examples, a liquid epoxy resin made by alkaline condensation of bis(4-oxyphenyl)-2,2-propane with epichlorhydrin is hardened (3) with BF3-acetoxime complex in diethylene glycol; (4) as in (3) after addition of fat alcohol glycidyl ether; (5) as in (3) and (4) with ethylene glycol monallyl ether as solvent; (7) with BF3-benzophenone oxime and polyethylene glycol monoethyl ether; (8) BF3-cyclohexanone oxime and diethylene glycol; (9) BF3-furfuraldoxime in diethylene glycol; (10) BF3-aldoxime and diethylene glycol monoethyl ether; (11) after dilution with fat alcohol glycidyl ether and phenylglycidyl ether with a polyamide and BF3-acetoxime in ethylene glycol; (12) after dilution as in (12) with diethylene triamine and BF3-acetoxime in ethylene glycol; (13) as in (12) using a cycloaliphatic diamine as co-hardener.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0062563 | 1961-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB967351A true GB967351A (en) | 1964-08-19 |
Family
ID=6973629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB18804/62A Expired GB967351A (en) | 1961-05-19 | 1962-11-16 | Improvements in and relating to the preparation of boron trifluoride-oxime complexes and the use of such complexes as hardeners for synthetic resins |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1445241A1 (en) |
| GB (1) | GB967351A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4079149A (en) * | 1977-06-30 | 1978-03-14 | Shell Oil Company | Benzyl oxime ethers |
| USRE30634E (en) * | 1979-08-27 | 1981-06-02 | Shell Oil Company | Benzyl oxime ethers |
| EP1266921A1 (en) * | 2000-05-30 | 2002-12-18 | Toray Industries, Inc. | Epoxy resin composition for fiber-reinforced composite material |
-
1961
- 1961-05-19 DE DE19611445241 patent/DE1445241A1/en active Pending
-
1962
- 1962-11-16 GB GB18804/62A patent/GB967351A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4079149A (en) * | 1977-06-30 | 1978-03-14 | Shell Oil Company | Benzyl oxime ethers |
| USRE30634E (en) * | 1979-08-27 | 1981-06-02 | Shell Oil Company | Benzyl oxime ethers |
| EP1266921A1 (en) * | 2000-05-30 | 2002-12-18 | Toray Industries, Inc. | Epoxy resin composition for fiber-reinforced composite material |
| EP1266921A4 (en) * | 2000-05-30 | 2003-04-16 | Toray Industries | Epoxy resin composition for fiber-reinforced composite material |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1445241A1 (en) | 1969-02-13 |
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