GB1036574A - New epoxide-containing metal chelates process for their preparation and their use - Google Patents
New epoxide-containing metal chelates process for their preparation and their useInfo
- Publication number
- GB1036574A GB1036574A GB2264763A GB2264763A GB1036574A GB 1036574 A GB1036574 A GB 1036574A GB 2264763 A GB2264763 A GB 2264763A GB 2264763 A GB2264763 A GB 2264763A GB 1036574 A GB1036574 A GB 1036574A
- Authority
- GB
- United Kingdom
- Prior art keywords
- radical
- compounds
- copper
- bis
- metal
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- 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
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
-
- 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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
-
- 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
- C08G59/30—Di-epoxy compounds containing atoms other than carbon, hydrogen, oxygen and nitrogen
-
- 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
- C08G59/70—Chelates
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
Abstract
Metal chelates containing epoxide groups are prepared by reacting an acetoacetic ester of the formula <F\1> where R1 and R2 each represents a hydrogen atom or alkyl radical with 1 to 4 carbon atoms, Z is an aliphatic, cyclo-aliphatic or araliphatic radical containing at least one 1,2-epoxide group or a radical differing from such a radical as aforesaid by containing in place or a methylene radical, a divalent functional radical and n is an integer, with a metal compound capable of forming stable chelate compounds with b -dicarbonyl compounds. Metal compounds specified are the halides, sulphates, nitrates and acetates, which may be hydrated, of Sc, Ti, V, Cr, Mn, Fe, Co, Ni, Zn, Cu, Al, Be, Ga, Mg, Ca, Sr, Ba, Y, Zr, Nb, Mo, Rb, Re, Pd, Hf, Ta, W, Rh, Os, In, Pt, Ce, Hg, Pb, Th, Sn, Bi and U; vanadyl, uranyl, copper-, nickel- and cobaltammines; aluminium ethylate, isopropylate and butylate; tetrabutyl titanate; tetraethylene glycol ortho-titanate; bis-(tributoxytitanoxy) ethane; chromium trisacetylacetonate; copper bisacetylacetonate; vanadyl bisacetylacetonate, copper ethyl acetoacetate and chromium ethyl acetoacetate. The acetoacetic esters containing epoxide groups are the reaction products of hydroxyepoxy compounds and diketeness. In the examples, the adducts of ketene with the indicated epoxides are reacted with the indicated metal compounds; (6) glycidol, tetrabutyl titanate; (7) ethylene glycol monoglycidyl ether, aluminium ethylate; (8) 3,4epoxyhexahydrobenzal glycerol, 1,2-bis-(tributoxytitanoxy) ethane; (9) 3,4 - epoxyhexahydrobenzal glycerol, MgCl2.6H2O; (10) 3,4epoxytetrahydrodicyclopentadienol - 8, 1,2-bis(tributyoxytitanoxy) ethane; (11) and (12) 3,4epoxytetrahydrodicyclopentadienol - 8, MgCl2. 6H2O; and (16) 3,4-epoxytetrahydicyclopentdienol-8, aluminium isopropylate. The preparation of the above mentioned ketene adducts, of ethylene glycol monoglycidyl ether, and of 1,2-bis-(tributoxytitanoxy) ethane are also described.ALSO:Metal chelates containing epoxide groups are prepared by reacting an acetoacetic ester of the formula <FORM:1036574/C3/1> where R1 and R2 each represents a hydrogen atom or an alkyl radical with 1 to 4 carbon atoms, Z stands for an aliphatic, cycloaliphatic or araliphatic radical containing at least one 1,2-epoxide group or a radical differing from such a radical as aforesaid by containing, in place of a methylene radical, a divalent functional radical and n is an integer, with a metal compound capable of forming stable chelate compounds with b -dicarbonyl compounds. Metal compounds specified are the halides, sulphates, nitrates and acetates which may be hydrated, of scandium titanium, vanadium, chromium, manganese, iron, cabalt, nickel, zinc, copper, aluminium, beryllium, gallium, magnesium, calcium, strontium, barium, yttrium, zirconium, niobium, molybdenum, rubidium, rhenium, palladium, hafnium, tantalum, tungsten, rhodium, osmium, indium, platinum, cerium, mercury, lead, thorium, tin, bismuth and uranium; vanadyl, uranyl, copper-, nickel- and cobalt-amines; aluminium ethylate, isopropylate and butylate; tetrabutyl titanate; tetraethylene glycol ortho-titanate; bis(tributoxy titanoxy)ethane; chromium trisacetylacetonate; copper bisacetylacetonate; vanadyl bis-acetylacetonate; copper ethyl acetoacetate and chromium ethyl acetoacetate. The acetoacetic esters containing epoxide groups are the reaction products of hydroxy-epoxy compounds and diketenes. The hydroxy-epoxy compounds may be polyepoxides or epoxy resins containing one or more hydroxyl groups which may have been introduced by the hydrolysis of epoxide groups; many such compounds are specified. The metal chelates formed may be cross-linked or cured by the conventional epoxy resin curing agents, many of which are specified, or they may be used as accelerators for the conventional epoxy resin curing agents in the curing of epoxy resins, many of which are specified. Curable mixtures containing the metal chelates may also contain asphalt, bitumen, glass fibres, mica, quartz meal, cellulose, kaolin, ground dolomite, colloidal silica, metal powder and solvents. They may be used as laminating resins, paints, lacquers, dipping and casting resins, moulding compositions, pore fillers, putties, floorings, potting and insulating materials for electrical components and as adhesives.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH688962 | 1962-06-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1036574A true GB1036574A (en) | 1966-07-20 |
Family
ID=4316652
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2264763A Expired GB1036574A (en) | 1962-06-07 | 1963-06-06 | New epoxide-containing metal chelates process for their preparation and their use |
Country Status (6)
Country | Link |
---|---|
AT (1) | AT242709B (en) |
BE (1) | BE633330A (en) |
DE (1) | DE1224743B (en) |
ES (1) | ES288799A1 (en) |
GB (1) | GB1036574A (en) |
NL (1) | NL293719A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3874903A (en) * | 1972-01-31 | 1975-04-01 | Reichhold Albert Chemie Ag | Epoxy resins |
US4016141A (en) * | 1971-07-30 | 1977-04-05 | Hoechst Aktiengesellschaft | Epoxy resin containing acetoacetic groups |
EP0974610A2 (en) * | 1998-07-21 | 2000-01-26 | HILTI Aktiengesellschaft | Curable epoxy compound and its use |
-
0
- NL NL293719D patent/NL293719A/xx unknown
- BE BE633330D patent/BE633330A/xx unknown
-
1963
- 1963-06-06 AT AT456263A patent/AT242709B/en active
- 1963-06-06 DE DEC30121A patent/DE1224743B/en active Pending
- 1963-06-06 ES ES288799A patent/ES288799A1/en not_active Expired
- 1963-06-06 GB GB2264763A patent/GB1036574A/en not_active Expired
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4016141A (en) * | 1971-07-30 | 1977-04-05 | Hoechst Aktiengesellschaft | Epoxy resin containing acetoacetic groups |
US3874903A (en) * | 1972-01-31 | 1975-04-01 | Reichhold Albert Chemie Ag | Epoxy resins |
EP0974610A2 (en) * | 1998-07-21 | 2000-01-26 | HILTI Aktiengesellschaft | Curable epoxy compound and its use |
EP0974610A3 (en) * | 1998-07-21 | 2000-02-23 | HILTI Aktiengesellschaft | Curable epoxy compound and its use |
US6214159B1 (en) | 1998-07-21 | 2001-04-10 | Hilti Aktiengesellschaft | Curable epoxide composition and its use |
AU764179B2 (en) * | 1998-07-21 | 2003-08-14 | Hilti Aktiengesellschaft | Curable epoxide composition and its use |
Also Published As
Publication number | Publication date |
---|---|
ES288799A1 (en) | 1963-11-16 |
AT242709B (en) | 1965-10-11 |
DE1224743B (en) | 1966-09-15 |
BE633330A (en) | |
NL293719A (en) |
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