Patent ID: 6599963
Filing Date: 2003-07-29
Classification: C07D,C08K,C09K

Abstract:
A flame retardant polymer composition which comprises(a) a polymer substrate, and (b) an effective flame retarding amount of a synergistic mixture of (i) a hindered amine and (ii) a brominated flame retardant; wherein said composition comprises essentially no antimony oxides, wherein the hindered amine of component (i) is selected from the group consisting of (A), (B) and (IIIb), wherein (A) is wherein E is alkoxy of 1 to 18 carbon atoms, cycloalkoxy of 5 to 12 carbon atoms or aralkoxy of 7 to 15 carbon atoms, or E is â€”Oâ€”Tâ€”(OH)b, T is a straight or branched chain alkylene of 1 to 18 carbon atoms, cycloalkylene of 5 to 18 carbon atoms, cycloalkenylene of 5 to 18 carbon atoms, a straight or branched chain alkylene of 1 to 4 carbon atoms substituted by phenyl or by phenyl substituted by one or two alkyl groups of 1 to 4 carbon atoms; b is 1, 2 or 3 with the proviso that b cannot exceed the number of carbon atoms in T, and when b is 2 or 3, each hydroxyl group is attached to a different carbon atoms of T; R is hydrogen or methyl, m is 1 to 4, when m is 1, R2 is hydrogen, C1-C18alkyl or said alkyl optionally interrupted by one or more oxygen atoms, C2-C12alkenyl, C6-C10aryl, C7-C18aralkyl, glycidyl, a monovalent acyl radical of an aliphatic, cycloaliphatic or aromatic carboxylic acid, or a carbamic acid, or wherein x is 0 or 1, or wherein y is 2-4; when m is 2, R2 is C1-C12alkylene, C4-C12alkenylene, xylylene, a divalent acyl radical of an aliphatic, cycloaliphatic, araliphatic or aromatic dicarboxylic acid or of a dicarbamic acid, or wherein D1 and D2 are independently hydrogen, an alkyl radical containing up to 8 carbon atoms, an aryl or aralkyl radical including 3,5-di-t-butyl-4-hydroxybenzyl radical, D3 is hydrogen, or an alkyl or alkenyl radical containing up to 18 carbon atoms, and d is 0-20; when m is 3, R2 is a trivalent acyl radical of an aliphatic, unsaturated aliphatic, cycloaliphatic, or aromatic tricarboxylic acid; when m is 4, R2 is a tetravalent acyl radical of a saturated or unsaturated aliphatic or aromatic tetracarboxylic acid including 1,2,3,4-butanetetracarboxylic acid, 1,2,3,4-but-2-enetetracarboxylic, and 1,2,3,5- and 1,2,4,5-pentanetetracarboxylic acid; wherein (B) is a mixture of N,Nâ€²,Nâ€²â€³-tris{2,4-bis[(1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidin-4-yl)alkylamino]-s-triazin-6-yl}-3,3â€²-ethylenediiminodipropylamine; N,Nâ€²,Nâ€³-tris{2,4-bis[(1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidin-4-yl)alkylamino]-s-triazin-6-yl}-3,3â€²-ethylenediiminodipropylamine IIA, and bridged derivatives as described by formulas I, II, and III R1NHâ€”CH2CH2CH2NR2CH2CH2NR3CH2CH2CH2NHR4â€ƒâ€ƒ(I) Tâ€”E1â€”T1â€ƒâ€ƒ(II) Tâ€”E1â€ƒâ€ƒ(IIA) Gâ€”E1â€”G1â€”E1â€”G2â€ƒâ€ƒ(III) where in the tetraamine of formula I R1 and R2 are the s-triazine moiety E; and one of R3 and R4 is the s-triazine moiety E with the other of R3 or R4 being hydrogen, E is R is methyl, propyl, cyclohexyl or octyl, R5 is alkyl of 1 to 12 carbon atoms, where in the compound of formula II or IIA when R is propyl, cyclohexyl or octyl, T and T1 are each a substituted by R1-R4 as is defined for formula I, where (1) one of the s-triazine moieties E in each tetraamine is replaced by the group E1 which forms a bridge between two tetraamines T and T1, E1 is or (2) the group E1 can have both termini in the same tetraamine T as in formula IIA where two of the E moieties of the tetraamine are replaced by one E1 group, or (3) all three s-triazine substituents of tetraamine T can be E1 such that one E1 links T and T1 and a second E1 has both termini in tetraamine T, L is propanediyl, cyclohexanediyl or octanediyl; where in the compound of formula III G, G1 and G2 are each tetraamines substituted by R1-R4 as defined for formula I, except that G and G2 each have one of the s-triazine moieties E replaced by E1, and G1 has two of the triazine moieties E replaced by E1, so that there is a bridge between G and G1 and a second bridge between G1 and G2; which mixture is prepared by reacting two to four equivalents of 2,4-bis[(1-hydrocarbyloxy-2,2,6,6-piperidin-4-yl)butylamino]-6-chloro-s-triazine with one equivalent of N,Nâ€²-bis(3-aminopropyl)-ethylenediamine; and wherein (IIIb) is in which the index n ranges from 1 to 15; R12 is C2-C12alkylene, C4-C12alkenylene, C5-C7cycloalkylene, C5-C7cycloalkylene-di(C1-C4alkylene), C1-C4alkylenedi(C5-C7cycloalkylene), phenylenedi(C1-C4alkylene) or C4-C12alkylene interrupted by 1,4-piperazinediyl, â€”Oâ€” or >Nâ€”X1 with X1 being C1-C12acyl or (C1-C12alkoxy)carbonyl or having one of the definitions of R14 given below except hydrogen; or R12 is a group of the formula (Ibâ€²) or (Icâ€²); with m being 2 or 3, X2 being C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl or C1-C4alkoxy; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; and the radicals X3 being independently of one another C2-C12alkylene; R13, R14 and R15, which are identical or different, are hydrogen, C1-C18alkyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; C3-C18alkenyl, phenyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl or C1-C4alkoxy; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; tetrahydrofurfuryl or C2-C4alkyl which is substituted in the 2, 3 or 4 position by â€”OH, C1-C8alkoxy, di(C1-C4alkyl)amino or a group of the formula (Ieâ€²); with Y being â€”Oâ€”, â€”CH2â€”, â€”CH2CH2â€” or >Nâ€”CH3, or â€”N(R14(R15) is additionally a group of the formula (Ieâ€²); the radicals A are independently of one another â€”OR13, â€”N(R14(R15) or a group of the formula (IIId); X is â€”Oâ€” or >Nâ€”R16; R16 is hydrogen, C1-C18alkyl, C3-C18alkenyl, C5-C12cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C1-C4alkyl; C7-C9phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C1-C4alkyl; tetrahydrofurfuryl, a group of the formula (IIIf), or C2-C4alkyl which is substituted in the 2, 3 or 4 position by â€”OH, C1-C8alkoxy, di(C1-C4alkyl)amino or a group of the formula (Ieâ€²); R11 has one of the definitions given for R16; and the radicals B have independently of one another one of the definitions given for A; with the proviso that when the polymer substrate is polypropylene, the flame retardant is not a halogenated hydrocarbyl phosphate or phosphonate.