EP0000763A1 - Glycidylaminoéthers et procédé pour leur préparation - Google Patents

Glycidylaminoéthers et procédé pour leur préparation Download PDF

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Publication number
EP0000763A1
EP0000763A1 EP78100563A EP78100563A EP0000763A1 EP 0000763 A1 EP0000763 A1 EP 0000763A1 EP 78100563 A EP78100563 A EP 78100563A EP 78100563 A EP78100563 A EP 78100563A EP 0000763 A1 EP0000763 A1 EP 0000763A1
Authority
EP
European Patent Office
Prior art keywords
epichlorohydrin
alkylene groups
groups containing
general formula
atoms
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.)
Withdrawn
Application number
EP78100563A
Other languages
German (de)
English (en)
Inventor
Rainer Dr. Strickler
Knut Dr. Oppenlaender
Karl Dr. Merkel
Erich Dr. Penzel
Robert Dr. Fischer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP0000763A1 publication Critical patent/EP0000763A1/fr
Withdrawn legal-status Critical Current

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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
    • C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms

Definitions

  • Tetraglycidyl compounds can be produced using the usual hardener epoxy resins with relatively good temperature resistance.
  • X means only the 2,3-epoxypropyl radical and R 1 preferably represents alkylene groups containing 2 to 3 carbon atoms, in particular trimethyl groups, R 2 preferably represents alkylene groups containing 2 to 6 carbon atoms, in particular the ethylidene, trimethylene, tetramethylene, pentamethylene and / or hexamethylene radical , and n for preferably 0 to 15.
  • Suitable ether diamines (II) for the preparation of the glycidyl ether amines (I) are, for example, 4,7,10-trioxatridecane-1,13-diamine, 4,7-dioxadecane-1,10-diamine , 4,9-dioxadodecane-1,12-diamine, 4-oxaheptane-1,7-diamine and 4,11-dioxatetradecane-1,14-diamine, 4-oxaheptane-1,7-diamine, 4,11 -Dioxatetradecan-1,14-diamine and the etheramine of the general formula H 2 NC 3 H 6 C (C 4 H 8 O) 9 ' C 3 H 6 NH 2 .
  • the reaction of the ether amines (II) with epichlorohydrin is generally carried out at temperatures from 25 to 40, preferably at 30 to 35 ° C. in the presence of traces of water. In general, at least about 0.5, in particular 1%, water, based on the amount of theramine (II), should be present and the temperature should not reach 50 ° C. in order to prevent the formation of undesired polycondensation products.
  • the concentration of epichlorohydrin in the solvent can be varied within wide limits. It is usually between 0.1 and 25%, preferably between 0.5 and 5% by weight, based on the solution.
  • the ether diamine (II), optionally in the form of its solution, is added to the solution of the epichlorohydrin in a solvent of the type mentioned, ie one Allow alkanol and / or water to flow in, usually cooling.
  • the reaction temperature optionally by cooling below 50 ° C, preferably between 0 ° and 4 0 0, in particular between 20 and 30 ° C.
  • the glycidyl ether amines can be extracted from the reaction mixture using, for example, liquid hydrocarbons such as benzene, pentane or toluene or ethers such as diethyl ether and diisobutyl ether. After drying, the glycidyl ether amines can be obtained from the extract as a residue, for example by evaporating the extractant (ether or hydrocarbon).
  • Their yield, based on the ether diamine (II) used is generally between 50 and 80% of theory and the products can be stored for several weeks at temperatures up to 20 ° C., in particular with the addition of customary stabilizing agents, without decomposition. For storage it is advantageous to store the glycidyl ether amines as a solution in dioxane or ethylene glycol dimethyl ether.
  • the glycidyl ether amines are generally low-viscosity, colorless to light yellow oils. They are easily soluble in many organic solvents, e.g. in benzene, toluene, tetrahydrofuran, dioxane, methyl alcohol, ethyl alcohol, cyclohexanone and dimethylformamide.
  • the glycidyl ether amines are mostly water-soluble, especially if their carbon number in the radical R 2 is not more than 2. They react with amino, alcohol, carboxylic acid, anhydride and phenol groups.
  • They are suitable, for example, as crosslinking agents for polymers having coreactive groups and thereby outperform the diglycidylamines derived from primary aliphatic amines, such as n-butyl-bis-glycidylamine. They can also be used as a means for regulating the consistency of screen printing inks, especially based on ethylene glycol.
  • the new aliphatic tetraglycidyl ether amines are significantly more reactive and less sensitive to light than the araliphatic tetraglycidyl ether amines of US Pat. No. 3,312,664. In addition, they outperform the tetraglycidyl compounds of US Pat. No. 3,312,664 in their water solubility, which is advantageous in many reactions.
  • the parts given in the following examples are parts by weight.
  • the parts of volume specified therein behave like liters to kilograms.
  • a mixture of 378 parts of epichlorohydrin and 50 parts by volume of water is placed in a reaction vessel equipped with a thermometer, feed vessel and stirrer.
  • the mixture is cooled from the outside with ice water and 240 parts of 4,7,10-trioxatridecane-1,13-diamine (degree of purity 91%) are metered in such that the temperature of the reaction mixture remains between 30 and 35 ° C.
  • stirring is continued for 4 hours after the addition of the diamine until the epoxy oxygen content of the reaction solution has dropped below 0.4%.
  • the mixture is then diluted with 200 parts by volume of isopropanol and a total of 400 parts by volume of 50% strength aqueous sodium hydroxide solution Over half an hour at 20 to 25 ° C.
  • the mixture is then stirred for a further 2 hours, filtered off with sodium chloride and extracted twice with 500 parts by volume of toluene.
  • the combined toluene extracts are dried over potassium hydroxide, then over magnesium sulfate.
  • the toluene is evaporated off from the dried extracts at 60 ° C. under reduced pressure.
  • the residue obtained is 322 parts of a mixture of N-glycidyl compounds of 4,7,10-trioxatridecane-1,13-diamine, which, as can be seen from the information on the poxide content in the following table, predominantly from tetraglycidyl-4 , 7,10-trioxatridecan-1113-diamine.
  • the corresponding tetraglycidyl ether amines were isolated from the reaction products of Examples 2 and 3 by liquid chromatography (gel permeation) on a Merkogel OR-PVA-2000 column with tetrahydrofuran as the eluent and a differential refractometer as the detector.
  • tetraglycidyl-4,6-dioxadecane-1,10-diamine with an epoxide O content of 15.5% (theory 15.8) and nitrogen content 6.7% (theory 6.9%) found; 30% of the product consisted of higher molecular components, which also contained epoxy.
  • the main component was isolated using preparative liquid chromatography to determine epoxide and nitrogen.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Compounds (AREA)
  • Epoxy Resins (AREA)
EP78100563A 1977-08-09 1978-08-01 Glycidylaminoéthers et procédé pour leur préparation Withdrawn EP0000763A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2735765 1977-08-09
DE19772735765 DE2735765A1 (de) 1977-08-09 1977-08-09 Glycidylaetheramine und verfahren zu ihrer herstellung

Publications (1)

Publication Number Publication Date
EP0000763A1 true EP0000763A1 (fr) 1979-02-21

Family

ID=6015931

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100563A Withdrawn EP0000763A1 (fr) 1977-08-09 1978-08-01 Glycidylaminoéthers et procédé pour leur préparation

Country Status (4)

Country Link
EP (1) EP0000763A1 (fr)
JP (1) JPS5436209A (fr)
DE (1) DE2735765A1 (fr)
IT (1) IT7850603A0 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0265753A1 (fr) * 1986-10-13 1988-05-04 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Composés glycidylés et leur procédé de préparation
US4908459A (en) * 1988-04-28 1990-03-13 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Glycidyl sulfonamide compound
EP0287249B1 (fr) * 1987-04-03 1992-03-04 Mitsubishi Gas Chemical Company, Inc. Procédé de préparation de composé polyglycidylamine

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3045805A1 (de) * 1980-12-05 1982-07-08 Basf Ag, 6700 Ludwigshafen Diphenylether, verfahren zu ihrer herstellung und ihre verwendung als herbizide

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB745499A (en) * 1952-12-02 1956-02-29 Bayer Ag Treatment of paper
CH396034A (fr) * 1959-03-06 1965-07-31 Union Carbide Corp Procédé de préparation de dérivés glycidyliques d'amino-phénols

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1132146B (de) 1954-12-06 1962-06-28 Bayer Ag Verfahren zur Herstellung von basischen aliphatischen N-Diepoxyden
US2963482A (en) 1957-09-09 1960-12-06 Lilly Co Eli Bis-epoxypropyldiamines
US3278561A (en) 1962-06-15 1966-10-11 Monsanto Co Hydrophobic diglycidylamines
US3312664A (en) 1964-07-02 1967-04-04 Dow Chemical Co Epoxylated aminomethyldiphenyloxides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB745499A (en) * 1952-12-02 1956-02-29 Bayer Ag Treatment of paper
CH396034A (fr) * 1959-03-06 1965-07-31 Union Carbide Corp Procédé de préparation de dérivés glycidyliques d'amino-phénols

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0265753A1 (fr) * 1986-10-13 1988-05-04 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Composés glycidylés et leur procédé de préparation
US4847395A (en) * 1986-10-13 1989-07-11 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Glycidyl compounds
EP0287249B1 (fr) * 1987-04-03 1992-03-04 Mitsubishi Gas Chemical Company, Inc. Procédé de préparation de composé polyglycidylamine
US4908459A (en) * 1988-04-28 1990-03-13 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Glycidyl sulfonamide compound
US4975511A (en) * 1988-04-28 1990-12-04 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Glycidyl sulfonamide compound

Also Published As

Publication number Publication date
DE2735765A1 (de) 1979-02-22
JPS5436209A (en) 1979-03-16
IT7850603A0 (it) 1978-08-04

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Inventor name: PENZEL, ERICH, DR.

Inventor name: STRICKLER, RAINER, DR.

Inventor name: OPPENLAENDER, KNUT, DR.

Inventor name: MERKEL, KARL, DR.

Inventor name: FISCHER, ROBERT, DR.