N,N'substituted 2,4,5-triketoimidazolidines, corresponding resinous polymers and a process for their preparation

A process for the preparation of a compound of the general formula ##STR38## wherein one of Q and Q' are independently the group --NH--CO--OR.sup.IV or hydrogen and the other --NH--CO--COOR.sup.V or hydrogen, wherein

• R.sup.iv and R.sup.V are aliphatic hydrocarbon groups with up to 18 carbon atoms, cycloaliphatic hydrocarbon groups with up to 8 carbon atoms, mononuclear aromatic hydrocarbon groups with 6 carbon atoms, or such mononuclear aromatic groups of 6 carbon atoms substituted with hydrocarbon groups having up to 14 carbon atoms, an urethane or an isocyanate group;
• R''' is an aromatic radical phenyl, naphthyl, phenylene, naphthylene that are unsubstituted or monosubstituted with nitro, halo, lower alkyl, lower alkoxy or haloalkyl, or an unsubstituted alkylene radical having up to 6 carbon atoms,
• A is one of the radicals
• I) r' which is ##STR39## and that is unsubstituted or monosubstituted with lower alkyl, lower alkoxy, halo, nitro, or haloalkyl wherein X is a bond, CH.sub.2, O, S or sulphonylene, and
• Ii) r'''
• and wherein the radicals being arranged between the imidazolidine rings in the chain always are alternatively R' derived from an oxamidic acid ester and R''' derived from an isocyanate and the various radicals R' and R''' in one chain have per se the same or different meaning, wherein the radical A being bound to the terminal radical Q is always R',
• z is 2,
• and wherein at least one of A and R''' is a m-methylbenzothiazolyl radical which comprises reacting at least one oxamidic ester with the grouping --NH--CO--CO--OR.sup.V with an isocyanate or a corresponding isocyanate-forming compound, and wherein the reaction components are at most bi-functional, at temperatures of -20.degree. to +280.degree. C in the presence or absence of a catalyst in a ratio of
• a. a diisocyanate:a bis-oxamidic ester of about (1 to 2):1 or
• b. a diisocyanate:a bis-oxamidic ester of about (1 to 2):1 with a subsequent heating of the product at a temperature in the range from 200.degree. to 250.degree. C.

A process for the preparation of a compound of the general formula ##STR45## wherein one of C and Q' are independently the group --NH--CO--OR.sup.IV or hydrogen and the other --NH--CO--COOR.sup.V or hydrogen, wherein

• R.sup.iv and R.sup.V are aliphatic hydrocarbon groups with up to 18 carbon atoms, cycloaliphatic hydrocarbon groups with up to 8 carbon atoms, mononuclear aromatic hydrocarbon groups with 6 carbon atoms, or such mononuclear aromatic groups of 6 carbon atoms substituted with hydrocarbon groups having up to 14 carbon atoms, an urethane or an isocyanate group;
• R''' is an aromatic radical phenyl, naphthyl, phenylene, naphthylene that are unsubstituted or monosubstituted with nitro, halo, lower alkyl, lower alkoxy or haloalkyl, or an unsubstituted alkylene radical having up to 6 carbon atoms,
• A is one of the radicals
• I) r' which is ##STR46## and that is unsubstituted or monosubstituted with lower alkyl, lower alkoxy, halo, nitro, or haloalkyl wherein X is a bond, CH.sub.2, O, S or sulphonylene, and
• Ii) r'''
• and wherein the radicals being arranged between the imidazolidine rings in the chain always are alternatively R' derived from an oxamidic acid ester and R''' derived from an isocyanate and the various radicals R' and R''' in one chain have per se the same or a different meaning, wherein the radical A being bound to the terminal radical Q is always R',
• z is 2,
• and wherein at least one of A and R''' is a m-methylbenzothiazolyl radical which comprises reacting at least one oxamidic ester with the grouping --NH--CO--CO--OR.sup.V with an isocyanate or a corresponding isocyanate-forming compound, and wherein the reaction components are at most bi-functional, at temperatures of -20.degree. to +280.degree. C in the presence or absence of a catalyst in a ratio of
• a. a diisocyanate:
• a bis-oxamidic ester of about (1 to 2) :
• 1 or
• b. a diisocyanate:
• a bis-oxamidic ester of about (1 to 2) :
• 1 with a subsequent heating of the product at a temperature in the range from 200.degree. to 250.degree. C.

A compound of the general formula ##STR48## wherein one of Q and Q' are independently the group --NH--CO--OR.sup.IV or hydrogen and the other --NH--CO--COOR.sup.V or hydrogen, wherein

• R.sup.iv and R.sup.V are aliphatic hydrocarbon groups with up to 18 carbon atoms, cycloaliphatic hydrocarbon groups with up to 8 carbon atoms, mononuclear aromatic hydrocarbon groups with 6 carbon atoms, or such mononuclear aromatic groups of 6 carbon atoms substituted with hydrocarbon groups having up to 14 carbon atoms, an urethane or an isocyanate group;
• R''' is an aromatic radical phenyl, naphthyl, phenylene, naphthylene that are unsubstituted or monosubstituted with nitro, halo, lower alkyl, lower alkoxy or haloalkyl, or an unsubstituted alkylene radical having up to 6 carbon atoms,
• A is one of the radicals
• I) r' which is ##STR49## and that is unsubstituted or monosubstituted with lower alkyl, lower alkoxy, halo, nitro, or haloalkyl wherein X is a bond, CH.sub.2, O, S or sulphonylene, and
• Ii) r'''
• and wherein the radicals being arranged between the imidazolidine rings in the chain always are alternatively R' derived from an oxamidic acid ester and R''' derived from an isocyanate and the various radicals R' and R''' in one chain have per se the same or a different meaning, wherein the radical A being bound to the terminal radical Q is always R',
• z is 2.