Triazine derivatives and a method for their production

A method for the production of triazine derivatives of general formula (I),

• wherein
• R3′ means Q1 or a moiety of the formula R5′—N—R6′ connected with the nitrogen atom to the triazine ring of the structure of formula (I), wherein
• Q1 means a linear or branched C1-C50-alkyl or a cyclic substituent in the form of a C5-C20-cycloalkyl, a C5-C20-aryl, a C1-C20-alkyl substituted C5-C20-aryl, a C2-C20-alkenyl substituted C5-C20-aryl or of an imide of a cyclic saturated or unsaturated carboxylic acid, wherein the C1-C50-alkyl or the cyclic substituent can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
• R4′ means Q1 or a moiety of the formula R7′—N—R8′ connected with the nitrogen atom to the triazine ring of the structure of the formula (I),
• R1′, R5′, and R7′ mean independently from each other H or Q2, wherein
• Q2 means in each case a linear or branched C1-C50-alkyl, C5-C20-cycloalkyl, C5-C20-aryl, C1-C20-alkyl substituted C5-C20-aryl, C2-C20-alkenyl or C2-C20-alkenyl substituted C5-C20-aryl, that in each case can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
• A′ means —O—, —NH—, —NR2′—, —NR62′— or —NR82′—,
• R6′ and R8′ mean independent from each other means H, Q2-CO-A-R2′, —CO-A-R61′, —CO-A-R81′,
• R2′, R61′, R62′, R81′ and R82′ mean independent from each other Q2, a moiety of a substituted or non-substituted alcohol, a moiety of a substituted or unsubstituted polyvalent alcohol, a moiety of an amine, moiety of an amino alcohol, a moiety of a diamine or a moiety of the general formula (II),
• whereby R9′ means Q2,
• with the stipulation that in case R3′ means R5′—N—R6′ and R4′ means R7′—N—R8′,
• at least one of the moieties R1′, R5′, and R7′ means Q2 and is bound to a nitrogen atom that is covalently connected to the moiety —CO-A-R2′, —CO-A-R61′ or —CO-A-R81′, or
• at least the moieties R5′ and R6′ on the one hand and the moieties R7′ and R8′ on the other hand mean in each case Q2 or
• at least one of the moieties R5′ or R6′ means Q2 and R7′ and R8′ mean both simultaneously H,
• or mixtures thereof,
• comprising the steps of:
• A) converting a triazine derivative according to the general formula (IX)
• whereby
• R3′ means Q1 or a moiety of the formula R5′—N—R6′ bound with its central nitrogen atom to the triazine ring of the structure of the formula (IX), wherein
• Q1 means a linear or branched C1-C50-alkyl or a cyclic substituent in the form of a C5-C20-cycloalkyl, a C5-C20-aryl, a C1-C20-alkyl substituted C5-C20-aryl, a C2-C20-alkenyl substituted C5-C20-aryl or an imide of cyclic saturated or unsaturated carboxylic acids, wherein the C1-C50-alkyl or the cyclic substituent can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
• R4′ means Q1 or a moiety of the formula R7′—N—R8′ bound with the nitrogen atom to the triazine ring of the structure of the formula (IX),
• R1′, R5′, and R7′ independently from each other mean H or Q2, wherein
• Q2 means in each case linear or branched C1-C50-alkyl, C5-C20-cycloalkyl, C5-C20-aryl, C1-C20-alkyl substituted C5-C20-aryl, C2-C20-alkenyl or C2-C20-alkenyl substituted C5-C20-aryl, which can be interrupted in each case by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
• R6′ and R8′ mean independently from each other H, Q2, —CO-A-R61′ or —CO-A-R81′,
• A′ means —O—, —NH— —CO-A-R62′ or —CO-A-R82′,
• R61′, R62′, R81′ and R82′ mean independently from each other Q2, a moiety of a substituted or unsubstituted alcohol, a moiety of the substituted or unsubstituted polyvalent alcohol, a moiety of an amine, a moiety of an amino alcohol, a moiety of a diamine or a moiety of the general formula (II),
• Whereby R9′ means Q2,
• with phosgen and
• B) converting the carbamoylchloride of the triazine derivative formed in step A) with a substituted or unsubstituted alcohol of the general formula R2, —OH, a substituted or unsubstituted polyvalent alcohol of the general formula R2′-(OH)n with n≧2, an amine of the general formula R2′—NH2 or R2′—NH—R20′, an amino alcohol of the general formula OH—R2′—NH2 or R2′—NH—R20′—OH, a diamine of the general formula R2′, —(NH2)2 or a moiety of the general formula (II),
• whereby R2′ and R20′ mean independently from each other Q2, a moiety of a substituted or unsubstituted alcohol, a moiety of a substituted or unsubstituted polyvalent alcohol, a moiety of an amine, a moiety of an amino alcohol, a moiety of a diamine or a moiety of the general formula (II).

Triazine derivatives according to the general formula (Ib)

• wherein
• R3 means Q1 or a moiety of the formula R5—N—R6 connected with the nitrogen atom to the triazine ring of the structure of formula (Ib), wherein
• Q1 means a linear or branched C1-C50-alkyl or a cyclic substituent in the form of a C5-C20-cycloalkyl, a C5-C20-aryl, a C1-C20-alkyl substituted C5-C20-aryl, a C2-C20-alkenyl substituted C5-C20-aryl or of an imide of a cyclic saturated or unsaturated carboxylic acid, wherein the C1-C50-alkyl or the cyclic substituent can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
• R4 means Q1 or a moiety of the formula R7—N—R8 connected with the nitrogen atom to the triazine ring of the structure of the formula (Ib),
• R1, R5, and R7 mean independently from each other H or Q2, wherein
• Q2 means in each case a linear or branched C1-C50-alkyl, C5-C20-cycloalkyl, C5-C20-aryl, C1-C20-alkyl substituted C5-C20-aryl, C2-C20-alkenyl or C2-C20-alkenyl substituted C5-C20-aryl, that in each case can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted and/or unsubstituted nitrogen atoms and/or by one or multiple groups of the type —C(O)O—, —OC(O)—, —C(O)—, —NHC(O)O—, —OC(O)NH— and/or —OC(O)O—,
• A means —O—,
• R6 and R8 mean independent from each other H, Q2-CO-A-R2, —CO-A-R61, —CO-A-R81,
• R2, R61, R62, R81 and R82 mean independent from each other a moiety of a substituted or non-substituted alcohol selected from the compounds 2-hydroxyethylacrylate, 2-hydroxypropylacrylate, 4-hydroxybutylacrylate, 6-hydroxyhexyl-acrylate, diethylenglycolmonoacrylate, triethylenglycolmonoacrylate, dipropylenglycol-mono acrylate, tripropylenglycol-monoacrylate, trimethylolpropandiacrylate, pentaerythrit-diacrylate, pentaerythrittriacrylate, 2-hydroxyethylmethacrylate, 2-hydroxypropylmeth-acrylate, 4-hydroxybutylmethacrylate, 6-hydroxyhexylmethacrylate, diethylenglycol-monomethacrylate, triethylenglycol-monomethacrylate, dipropylenglycolmonometh-acrylate, tripropylenglycol-monomethacrylate, trimethylolpropandimethacrylate, penta-erythritdimethacrylate, penta-erythrittrimethacrylate and/or 4-hydroxybutylvinylether or a moiety of the general formula (II),
• whereby R9 means Q2,
• with the stipulation that in case R3 means R5—N—R6 and R4 means R7—N—R8,
• at least one of the moieties R1, R5, and R7 means Q2 and is bound to a nitrogen atom that is covalently connected to the moiety —CO-A-R2, —CO-A-R61 or —CO-A-R81, or
• at least the moieties R5 and R6 on the one hand and the moieties R7 and R8 on the other hand mean in each case Q2 or
• at least one of the moieties R5 or R6 means Q2 and R7 and R8 mean both simultaneously H,
• or mixtures thereof.