Sulfenamides as flame retardants

A composition comprising

• (a) one or more flame retardant compound(s) of formula (I), wherein the compound of formula (I) is selected from a group consisting of compounds of formula (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig), (Ih), and (Ii)
• wherein
• L3 is selected from a group consisting of a bond, C1-10-alkylenyl, —(C═O)—, —O—(C═O)—, —(C═O)—O—, O, NH—(C═O)—, —(C═O)—NH—, NH, and NR20;
• each R1 and R2 is independently selected from a group consisting of H, S(═O)pR3, C1-30-alkyl, C3-7-cycloalkyl optionally substituted one or more times with R10, C2-30-alkenyl, C2-30-alkynyl, C1-10-alkylenyl-X—C1-20-alkyl, C1-10-alkylenyl-X—C1-7-cycloalkyl optionally substituted one or more times with R10, a saturated or partly unsaturated mono- or bicyclic heterocycle optionally substituted one or more times with R10, and a mono- or bicyclic aryl or heteroaryl optionally substituted one or more times with R10;
• or
• R1, and R2 together with the N atom they are attached to form a NR1R2 group selected from a group consisting of a saturated or partly unsaturated mono- or bicyclic heterocycle optionally substituted one or more times with R10;
• a mono-, bi-, tri-, tetra- or pentacyclic heteroaryl optionally substituted one or more times with R10;
• N═CR1′R2′;
• and N=S=S;
• R3 is selected from a group consisting of C1-30-alkyl, C3-7-cycloalkyl optionally substituted one or more times with R30, C2-30-alkenyl, C2-30-alkynyl, NR1R2, a saturated or partly unsaturated mono- or bicyclic heterocycle optionally substituted one or more times with R30, and a mono-, bi-, or tricyclic aryl or heteroaryl optionally substituted one or more times with R30;
• or
• L3, R1, and R3 together with the N atom and the S atom they are attached to form a group selected from a mono-, bi-, or tricyclic heteroaryl optionally substituted one or more times with R40, and a saturated or partly unsaturated mono- or bicyclic heterocycle optionally substituted one or more times with R40;
• and R2 is as defined above;
• or
• L3, R1, R2, and R3 together with the S atom and the N atom to which they are attached to form a mono-, bi- or tricyclic heteroaryl optionally substituted one or more times with R50;
• each R1′ and R2′ is independently R1 or R2, respectively, as defined above, or R1′ and R2′ form together with the C atom they are attached to a CR1′R2′ group selected from a group consisting of a C3-7-cycloalkyl optionally substituted one or more times with R10, a saturated or partly unsaturated mono- or bicyclic heterocycle optionally substituted one or more times with R10, a mono- or bicyclic aryl or heteroaryl optionally substituted one or more times with R10,
• each R10 is independently selected from a group consisting of NO2, CN, SO3H, COOH, COOR20, CHO, COR20, OCOR20, O(C═O)O—(NR1″R2″)-S(═O)pR3, ═O, ═S, R20, NHCOR20, NH2, NHR20, N(R20)2, OH, OR20, OSiH3, OSi(R20)3, S(═O)pR3, ═N—S(═O)pR3, —N═N—(R1″R2″N)—S(═O)pR3, and ═N—N═(R1″R2″N)—S(═O)pR3, wherein R1″R2″N forms a monocyclic saturated heterocycle optionally substituted with one or more R10′;
• provided that when R10 is O(C═O)O—(NR1″R2″)-S(═O)pR3, S(═O)pR3, ═N—S(═O)pR3, —N═N—(R1″R2″N)—S(═O)pR3, or ═N—N═(R1″R2″N)— S(═O)pR3, the R3 is not substituted with NR1R2 or SNR1R2;
• each R10′ is independently selected from a group consisting of NO2, CN, SO3H, COOH, COOR20, CHO, COR20, OCOR20, ═O, R20, NHCOR20, NH2, NHR20, N(R20)2, OH, OR20, OSiH3, and OSi(R20)3;
• each R20 is independently selected from a group consisting of C1-30-alkyl, C2-30-alkenyl, C2-30-alkynyl, aryl, C1-10-alkylenyl-aryl, heteroaryl, and C1-10-alkylenyl-heteroaryl, wherein the aryl or heteroaryl is optionally substituted one or more times with C1-4-alkyl, NO2, CN, NH2, NMe2, OH and/or OMe;
• each R30 is independently selected from a group consisting of NO2, CN, SO3H, COOH, COOR20, CHO, COR20, OCOR20, ═O, R20, OH, OR20, OSiH3, OSi(R20)3, NHCOR20, NR1R2, and S(═O)p—NR1R2, provided that when R30 is NR1R2 or S(═O)p—NR1R2 the NR1R2 is not substituted with O(C═O)O—(NR1″R2″)-S(═O)pR3, S(═O)pR3, ═N—S(═O)pR3, —N═N—(R1″R2″N)—S(═O)pR3, or ═N—N═(R1″R2″N)—S(═O)pR3;
• each R40 is independently selected from a group consisting of NO2, CN, SO3H, COOH, COOR20, CHO, COR20, OCOR20, ═O, R20, OH, OR20, OSiH3, OSi(R20)3, NHCOR20, NR1R2, S(═O)pR3 and a saturated or partly unsaturated monocyclic heterocycle optionally substituted one or more times with R10′, provided that when R40 is NR1R2 or S(═O)pR3 the R3 is not substituted with NR1R2 or S(═O)p—NR1R2 and the NR1R2 is not substituted with O(C═O)O—(NR1″R2″)-S(═O)pR3, —S(═O)pR3, ═N—S(═O)pR3, —N═N—(R1″R2″N)—S(═O)pR3, or ═N—N═(R1″R2″N)—S(═O)pR3;
• each R50 is independently selected from a group consisting of NO2, CN, SO3H, COOH, COOR20, CHO, COR20, OCOR20, ═O, R20, OH, OR20, OSiH3, OSi(R20)3, NHCOR20, NR1R2, S(═O)pR3, and a saturated or partly unsaturated monocyclic heterocycle optionally substituted one or more times with R10′, provided that when R50 is NR1R2 or S(═O)pR3 the R3 is not substituted with NR1R2 or S(═O)p—NR1R2 and the NR1R2 is not substituted with O(C═O)O—(NR1″R2″)-S(═O)pR3, S(═O)pR3, ═N—S(═O)pR3, —N═N—(R1″R2″N)—S(═O)pR3, or ═N—N═(R1″R2″N)—S(═O)pR3;
• and
• each p is independently selected from the group consisting of 0, 1 and 2;
• each m is independently 0, 1, 2, 3, or 4,
• n is from 0 to 8,
• X′ is a bond, N or O, Z is selected from a group consisting of a bond, O, S, NH, NR20, N—SR3, CH2, CHR20, C(R20)2, and C═O,
• A is S, O or NH, and
• Y is selected from the group consisting of a bond, CH2, CHR10, C(R10)2, N—SR3, C═O, C═N—SR3, and C═N—N(R1″R2″N)—SR3,
• (b) a polymeric substrate,
• wherein the composition is free of a halogenated flame retardant, and
• and R1, R2, R3, R10, R20, R30, R40 and R50 are as defined above.