Ciba-Geigy Corporation

Ciba-Geigy Ag

Daniel Porret

Jurgen Habermeier

Hans Batzer

Juergen Habermeier

Dieter Baumann

Willy Fatzer

Juerger Habermeier

New dialcohols of mononuclear, five-membered or six-membered, unsubstituted or substituted N-heterocyclic compounds which contain two NH-groups in the molecule, by reaction of mononuclear, five-membered or six-membered, unsubstituted or substituted N-heterocyclic compounds, for example hydantoin, barbituric acid, uracil, dihydrouracil, parabanic acid and the corresponding derivatives, with ethylene oxide or propylene oxide to give dialcohols. These diols are useful as intermediates for the preparation of polymers, such as polyesters or polyurethanes, or of epoxy resins.

Dialcohols

New mono- or dialcohols of mononuclear, five-membered or six-membered, unsubstituted or substituted N-heterocyclic compounds which contain two NH-groups in the molecule, by reaction of mononuclear, five-membered or six-membered, unsubstituted or substituted N-heterocyclic compounds, for example hydantoin, barbituric acid, uracil, dihydrouracil, parabanic acid and the corresponding derivatives, with butene oxid, 1,2-cyclopentene oxide or 1,2-cyclohexene oxide to give monoalcohols or dialcohols. These compounds are useful as intermediates for the preparation of diglycidyl compounds as set forth in German Offenlegungsschrift No. 2,104,259.

Five- or six-membered heterocyclic mono -and dialcohols

The polyglycidyl compounds according to the invention can be manufactured by reacting epihalogenohydrin with compounds of the formula IV ##STR1## or the formula V ##STR2## in which (1) n denotes 2, 3 or 4, (2) A represents a 2-valent, 3-valent or 4-valent organic radical which either contains a N-heterocyclic or cycloaliphatic ring or 2 N-heterocyclic rings or 2 phenylene rings, (3) either D denotes the --CH.sub.2.O.CO-- radical and m denotes the number 1, or D denotes the radical ##STR3## and m denotes O, and (4) R.sup.1 represents a divalent radical, which contains at least one hydantoin ring or uracil ring. During the reaction hydrogen halide splits off. From curable mixtures containing polyglycidyl compounds according to the invention and a curing agent such as hexahydrophthalic anhydride or phthalic anhydride are obtained products with good mechanical and electrical properties.

Polyglycidyl compounds containing N-heterocyclic structure

The invention relates to 3-dialkoxyphosphonoalkyl-dihydrouracils. These compounds are manufactured by reacting dihydrouracils substituted in the 3-position by a halogenalkyl group with a trialkyl phosphite. The compounds are useful as flame retardants which may be incorporated into polymeric materials or their starting substances.

Dialkoxyphosphonoalkyl derivatives of dihydrouracils

New mono- and dialcohols of binuclear, five-membered or six-membered, unsubstituted or substituted N-heterocyclic compounds, which contain two NH groups in the molecule, by reaction of binuclear, five-membered or six-membered, unsubstituted or substituted, N-heterocyclic compounds, such as bis-(hydantoin) or bis-(dihydrouracil) compounds, for example 1,1'-methylene-bis-(5,5-dimethylhydantoin), bis-(5,5-dimethylhydantoinyl-3)-methane or 1,1'-methylene-bis-(5,6-dihydrouracil) with ethylene oxide, for example ethylene oxide or propylene oxide, to give the corresponding monohydroxy or dihydroxy compounds. These compounds are useful as intermediates for forming diglycidyl ether resins as described in German Offenlegungsschrift No. 2,003,016.

Mono- and dialcohols of five or six membered N-heterocyclic compounds,

New diacrylates are obtained by a process in which oxalkylated uracils dihydrouracils are esterfied with acrylic acid and/or methacrylic acid, or transesterified with acrylic acid ester and/or methacrylic acid ester. The new diacrylates are low-viscous liquids, which can be easily processed by virtue of their consistency; and the polymerisates produced therefrom, are distinguished by good flexural strength and high transparency.

Diacrylic acid ester derivatives of uracil compounds

The polyglycidyl compounds according to the invention can be manufactured by reacting epihalogenohydrin with compounds of the formula IV ##STR1## or the formula V ##STR2## in which 1. N DENOTES 2, 3 OR 4,

The polyglycidyl compounds according to the invention can be manufactured by reacting epihalogenohydrin with compounds of the formula IV ##STR1## or the formula V ##STR2## in which 1.) n denotes 2, 3 or 4, 2.) A represents a 2-valent, 3-valent or 4-valent organic radical which either contains a N-heterocyclic or cycloaliphatic ring or 2 N-heterocyclic rings or 2 phenylene rings, 3.) either B denotes the --CH.sub.2.O.CO-- radical and m denotes the number 1, or B denotes the radical ##STR3## and m denotes 0, and 4.) R.sup.1 represents a divalent radical, which contains at least one hydrantoin ring or uracil ring. During the reaction hydrogen halide splits off. From curable mixtures containing polyglycidyl compounds according to the invention and a curing agent such as hexahydrophthalic anhydride or phthalic anhydride are obtained products with good mechanical and electrical properties.

Polyglycidyl compounds containing n-heterocyclic structure

1-Glycidyl-3-dialkoxyphosphonoalkyl-hydantoins and 1-glycidyl-3-dialkoxyphosphonoalkyl-dihydrouracils. These compounds are used as flame-retardant additives in plastics, especially as additives to epoxide resins.

Dialkoxyphosphonoalkyl derivatives of cyclicureides containing glycidyl

Adducts of polyglycidyl compounds and cyclic ureides containing dialkoxyphosphonomethyl groups, such as 3-dialkoxyphosphonomethylhydantoins or 3-dialkoxyphosphonomethyldihydrouracils, and the use of the adducts for the manufacture of flameproof epoxide resins.

Adducts of polyglycidyl compounds and dialkoxyphosphono-methyl

The invention relates to 3-dialkoxyphosphonoalkyl-hydantoins and 3-dialkoxyphosphonoalkyl-dihydrouracils. These compounds are manufactured by reacting the hydantoins or dihydroaracils substituted in 3-position by a halogenalkyl group with a trialkyl phosphite. They can be incorporated into polymeric materials or their starting substances and impart to them non-inflammability.

Dialkoxyphosphonoalkyl derivatives of cyclic ureides

The invention relates to new triglycidyl compounds of the formula: ##EQU1## wherein X represents a bivalent alkylene group required for the formation of a 5- or 6-membered heterocycle, and R represents hydrogen or an alkyl group having 1 to 4 carbon atoms. The new triglycidyl compounds are stable in storage and from them are obtained, after curing, synthetic materials having good mechanical strength and high dimensional stability under heat.

Heterocyclic triglycidyl compounds and process

Adducts of cyclic urea derivatives and dialkyl phosphites, containing glycidyl groups, for example adducts of a diglycidyl compound of hydantoins, substituted in the 5-position by alkyl groups or an alkylene group, and of diethyl phosphite or dimethyl phosphite. These adducts are used for the manufacture of flame-retarding plastics.

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Binningen, Switzerland

Daniel Porret