GB865314A - Preparation of polyglycidyl aromatic polyamines and resinous compositions made therefrom - Google Patents

Preparation of polyglycidyl aromatic polyamines and resinous compositions made therefrom

Info

Publication number
GB865314A
GB865314A GB36246/57A GB3624657A GB865314A GB 865314 A GB865314 A GB 865314A GB 36246/57 A GB36246/57 A GB 36246/57A GB 3624657 A GB3624657 A GB 3624657A GB 865314 A GB865314 A GB 865314A
Authority
GB
United Kingdom
Prior art keywords
polyamine
polyamines
alkali
epihalohydrin
excess
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
Application number
GB36246/57A
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.)
Union Carbide Corp
Original Assignee
Union Carbide Corp
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 Union Carbide Corp filed Critical Union Carbide Corp
Publication of GB865314A publication Critical patent/GB865314A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00Polycondensates 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
    • C08G59/18Macromolecules 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
    • C08G59/20Macromolecules 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
    • C08G59/22Di-epoxy compounds
    • C08G59/28Di-epoxy compounds containing acyclic nitrogen atoms

Abstract

Heat curable resinous compositions comprise a hardening agent and a polyglycidyl aromatic polyamine obtained by reacting 1 mol of an aromatic primary polyamine with at least 2 mols of an epihalohydrin for each primary amine group, in the substantial absence of alkali and at a temperature not in excess of 80 DEG C., reacting the resulting polyamine epihalohydrin with at least a storchiometric amount of alkali and recovering the resulting polyglycidyl polyamine. Suitable hardeners are polyhydric phenols, primary and secondary polyamines, polyamides, and polymercaptans. Suitable catalysts which may be present are alkalis, amines, and quaternary ammonium compounds. The hardener may be used in proportions from 0.7 to 1,3 of the stoichiometric proportions. The glycidyl derivatives may be mixed at temperatures from 25 DEG -100 DEG C. and the catalyst or hardener is added, either as such or in solution. The composition is poured into a mould and cured at temperatures from 25 DEG -200 DEG C. The polyglycidyl polyamines may be used in combination with epoxy ethers of polyhydric phenols having a 1,2-epoxy equivalency greater than one, e.g. the glycidyll ethers of bisphenols. Examples describe casting compositions using the tetraglycidyl derivative of 4, 41-diamino-diphenyl methane with (2) the diglycidyl ether of bisphenol A, methanolic KOH and bisphenol A; (3) diglycidyl aniline, methanolic KOH, and bisphenol A; (4) methanolic KOH and bisphenol A and (5) 4, 41-diamine diphenyl methane.ALSO:Polygycidyl aromatic polyamines having at least an 80% epoxy content are made by reacting 1 mol of an aromatic primary polyamine with at least 2 mols of an epihalohydrin for each primary amine group present in the polyamine, in the substantial absence of alkali and at a temperature not in excess of 80 DEG C., reacting the resulting polyamine epihalohydrin with at least a stoichiometric amount of alkali and recovering the resulting polyglycidyl polyamine. It is preferred to carry out the first step in the presence of water, using up to a 300% (molar) excess of epihalohydrin, the excess being distilled off under reduced pressure after completion of the first stage. It is advantageous to use 5 to 25% by weight excess of alkali in the second stage, usually as a 50% by weight aqueous solution. An organic solvent mixture, such as toluene-alcohol, may be present in the second step. Examples of suitable polyamines are m- and p-phenylene diamine, benzidene and 4, 41 diamine diphenyl methane. The polyglycyl polyamines may be used in the preparation of thermosetting casting compositions (see Group IV(a)).
GB36246/57A 1956-11-23 1957-11-21 Preparation of polyglycidyl aromatic polyamines and resinous compositions made therefrom Expired GB865314A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US865314XA 1956-11-23 1956-11-23

Publications (1)

Publication Number Publication Date
GB865314A true GB865314A (en) 1961-04-12

Family

ID=22199194

Family Applications (1)

Application Number Title Priority Date Filing Date
GB36246/57A Expired GB865314A (en) 1956-11-23 1957-11-21 Preparation of polyglycidyl aromatic polyamines and resinous compositions made therefrom

Country Status (1)

Country Link
GB (1) GB865314A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4540769A (en) * 1983-09-29 1985-09-10 Ciba-Geigy Corporation Preparation of N-glycidyl compounds
FR2668160A1 (en) * 1990-10-23 1992-04-24 Amoco Corp EPOXIDE RESIN FORMULATIONS FOR PREPARING MATRICES HAVING BETTER STORAGE IN STORAGE OR STORAGE.

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4540769A (en) * 1983-09-29 1985-09-10 Ciba-Geigy Corporation Preparation of N-glycidyl compounds
FR2668160A1 (en) * 1990-10-23 1992-04-24 Amoco Corp EPOXIDE RESIN FORMULATIONS FOR PREPARING MATRICES HAVING BETTER STORAGE IN STORAGE OR STORAGE.
GB2249095A (en) * 1990-10-23 1992-04-29 Amoco Corp Epoxy resin matrix formulations with improved storage stability

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