Patent DE-102008038941-A1 (DE)
Title: New N-substituted oxazolidine derivatives useful for preparing hydroxyalkylamino and polymeric hydroxyalkylamino derivatives for manufacturing e.g. high-performance composite materials for parts of automotives and electronics
Inventor: RAETZSCH MANFRED
IPC: C07D263/04
Filed: 2008-08-11
Abstract: N-Substituted oxazolidine derivatives (I) are new. N-Substituted oxazolidine derivatives of formula (I) are new. R3 : -H, -1-8C alkyl or 6-15C aryl; R6 : CH 2-CHR1-O-CO-1-8C-alkyl, -CH 2-CHR1-O-CO-CR5=CH 2, -CH 2-CHR1-O-CO-NH-1-8C-alkyl, -CH 2-CHR1-O-CO-NH-6-15C-aryl, -CO-O-1-8C-alkyl, -CO-CR5=CH 2, -CO-O-phenyl, -CO-NH-1-8C-alkyl, -CO-NH-6-15C-aryl, -CH 2-CHR1-O-CO-CH 2-CO-CH 3, -CH 2-CHR1-O-CO-CH 2-CO-O-1-12C-alkyl; and R1, R5 : 1-8C alkyl or H. Independent claims are included for: (1) the preparation of (I); (2) hydroxyalkylamino derivatives of formula (Y1-[A] m) (III); (3) the preparation of (III) comprising (d) reacting the N-substituted oxazolidine derivative with a compound (A) comprising urea, di-alkylurea, triazines such as melamine, melam, substituted melamine, preferably succinimidomelamine, phthalimidomelamine, alkylated melamine (preferably N,N-dimethylmelamine) or ammeline, guanamines such as benzoguanamine or acetoguanamine, and amides, preferably bi- or polyfunctional polyamides, polyureas and polyurethanes and phenols, preferably ortho- or para-substituted phenols, bisphenol and novolac, preferably novolac from ortho- or para-substituted phenols; (4) N-substituted bisoxazolidine derivatives of formula (IV); (5) the preparation of (IV) comprising (a) reacting alkanolamine compounds of formula (HN-(CH 2CHR1-OH) 2) (A) or (HNR2-CH 2-CHR1-OH) (B) with an aldehyde of formula (HC(R3)=O); (b) dehydrating formed methylol derivatives to give an oxazolidine derivative of formula (II); and (c1) reacting (II) with bifunctional compounds containing bifunctional dicarboxylic groups of formula (1-4C alkyl-O-CO-1-8C alkyl-CO-O-1-4C alkyl), (1-4C alkyl-O-CO-6-15C-aryl-CO-O-1-4C alkyl), (1-4C alkyl-O-CO-CH=CH-CO-O-1-4 alkyl) or their anhydrides, diisocyanates of formula (OCN-1-8C alkyl-NCO) or (OCN-6-15C-aryl-NCO), or organic carbonates of formula (1-4C alkyl-O-CO-O-1-4C alkyl), (1-4C alkyl-O-CO-O-phenyl), (phenyl-O-CO-O-phenyl) to give (IV); (6) polymeric hydroxyalkylamino derivatives of formula ([-Y1-B1-] p) (XIII); (7) the preparation of (XIII) comprising (d1) reacting the N-substituted bisoxazolidine derivative with a compound (A), where the amide is preferably polyamides, polyureas and polyurethanes; (8) a mixture comprising at least one derivative (III) and/or at least a derivative (XIII) and at least one additive comprising UV stabilizers in the form of radical stabilizers and/or UV absorbers, fillers, reinforcing fibers and/or radical initiators; and (9) the use of (III) and/or (XIII) and the mixture for manufacturing crosslinked semifinished products, molding materials or high-performance composite materials for highly stressed parts in automotives, mechanical engineering, electrical engineering and electronics. In formula (III), A : -CHR3-NR15-CH 2-CHR1-OR16; Y1 : hydroxy phenyl group of formula (a)-(d), triazine group of formula (e)-(h), (-N12-CO-NR12) (i), ((-C(O)-NX-R8-) m) (j), ((-O-C(O)-NX-R8-) m) (k) or ((-NX-C(O)-NX-R8-) m) (l); R1, R3, R5 : 1-8C alkyl or H; R8 : 1-8C alkyl or 6-15C-aryl; R10 : 1-3C-alkyl; R11 : H, 1-4C alkyl, C 6H 5, C 6H 4-OH or 1-3C-alkyl-C 6H 4OH; R12 : H, 1-4C alkyl, 6-15C-aryl or -CHR3-NR15-CH 2CHR1-OR16; R13 : 1-8C alkyl, C 6H 5or heterocyclic groups (A13) comprising pyrrolidine-2,5-dion-1-yl group of formula (m), pyrrolidine-2,5-dion-1-yl, 3-methylene-pyrrolidine-2,5-dion-1-yl, piperidine-2,6-dion-1-yl, hexahydro-isoindole-1,3-dion-2-yl, decahydro-benzo[f]isoindole-1,3-dion-2-yl, isoindole-1,3-dion-2-yl or benzo[f]isoindole-1,3-dion-2-yl; R14 : 1-8C alkyl or 6-15C-aryl; R15 : H, 1-4C alkyl, 6-15C-aryl or -CH 2-CHR1-OR16; R16 : H, 1-8C-alkyl, -CO-NH-(1-18C alkyl), -CO-CR5=CH 2, -CO-O-1-4C alkyl, -CO-O-6-15C-aryl, -CO-CH 2-CO-CH 3, -CO-CH 2-CO-O-(1-12C-alkyl) or -Si(1-8C alkyl) 3; R17 : 1-12C-alkyl or -CH=CH-1-10C alkyl; X : A or H; and m, o : 1-30, where the linkage between the units A and Y1 takes place by at least one N atom, when Y1 unit contains a N-atom substituent, the linkage is in ortho and/or para-position to the hydroxyl group of the hydroxyaromatics, when the Y1 unit includes a hydroxyaromatic substitute in these positions, and/or the linkage between the units A and Y1 takes place by at least one O atom, when Y1 unit contains a O-atom substituent. In formula (IV), R3 : -H, -1-8C alkyl or 6-15C aryl; R1 : 1-8C alkyl or H; R7 : CH 2-CHR1-O-CO-R8-C(O)-O-CHR1-CH 2-, -CH 2-CHR1-O-CO-O-CHR1-CH 2-, -CH 2-CHR1-O-CO-NH-R8-NH-CO-O-CHR1-CH 2-, -C(O)-, -C(O)-R8-C(O)-, -C(O)-NH-R8-NH-C(O)- or -1-8C-alkyl; and R8 : 1-8C alkyl, 6-15C aryl or -CH=CH-. In formula (A), (B) and (II), R1 : H or 1-8C alkyl; R2, R3 : H, 1-8C-alkyl or 6-15C-aryl; and R4 : H, 1-8C alkyl, 6-15C-aryl or CH 2-CHR1-OH. In formula (XIII), B1 : CHR3NR15-CH 2-CHR1-O-CO-R9-CO-O-CHR1-CH 2-NR15-CHR3, -CHR3-NR15-CH 2-CHR1-O-CO-NH-R9-NH-CO-O-CHR1-CH 2-NR15-CHR3, -CHR3-N(CH 2-CHR1-OR16)-CO-N(CH 2-CHR1-OR16)-CHR3- or -CHR3-N(CH2-CHR1-OR16)-R2-N(CH2-CHR1-OR16)-CHR3-; Y1 : groups (b)-(l); R1, R5 : 1-8C alkyl or H; R8, R9 : 1-8C alkyl or 6-15C-aryl; R11 : -H, -1-4C alkyl, -C 6H 5or -1-3C-alkyl-C 6H 4OH; R3, R12 : -H, -1-4C alkyl or -6-15C-aryl; R13 : 1-8C alkyl, -C 6H 5or heterocyclic groups (A13); R15 : H, 1-4C alkyl, -6-15C-aryl or -CH 2-CHR1-OR16; R16 : H, -1-8C-alkyl, -CO-NH-(1-18C alkyl), -CO-CR5=CH 2, -CO-O-1-4C alkyl, -CO-O-6-15C-aryl, -CO-CH 2-CO-CH 3, -CO-CH 2-CO-O-(1-12C-alkyl) or -Si(1-8C alkyl) 3; R17 : 1-12C-alkyl or -CH=CH-1-10C alkyl; X : A or H; m, o : 1-30; and p : 3-100, where the linkage between the units A and Y1 takes place by at least one nitrogen atom, when Y1 unit contains a N-atom substituent, the linkage is in ortho and/or para-position to the hydroxyl group of the hydroxyaromatics, when the Y1 unit includes a hydroxyaromatic substitute in these positions, and/or the linkage between the units A and Y1 takes place by at least one O atom, when Y1 unit contains a O-atom substituent. 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