×

Benzotriazoles containing α-cumyl groups substituted by heteroatoms and compositions stabilized therewith

  • US 6,451,887 B1
  • Filed: 08/03/2000
  • Issued: 09/17/2002
  • Est. Priority Date: 08/03/2000
  • Status: Expired due to Fees
First Claim
Patent Images

1. A compound of formula I, II or III embedded imagewhereinG1 is hydrogen or halogen, G2 is hydrogen, cyano, perfluoroalkyl of 1 to 12 carbon atoms, halogen, —

  • CO—

    G3, —

    COOG3, —

    CONHG3, —

    CON(G3)2, E3SO—

    , E3SO2

    , nitro, —

    P(O)(C6H5)2, —

    P(O)(OG3)2, embedded imageG3 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms, E1 is hydrogen, straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 24 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by 1 to 4 alkyl of 1 to 4 carbon atoms;

    or E1 is alkyl of 1 to 24 carbon atoms substituted by one or two hydroxy groups;

    or E1 is alkyl of 1 to 24 carbon atoms, alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more —

    OCOE11, —

    OE4, —

    NCO, —

    NHCOE11, or —

    NE7E8, or mixtures thereof, where E4 is straight or branched chain alkyl of 1 to 24 carbon atoms or straight or branched chain alkenyl of 2 to 18 carbon atoms;

    or said alkyl or said alkenyl interrupted by one or more —

    O—

    , —

    NH—

    or —

    NE4

    groups or mixtures thereof and which can be unsubstituted or substituted by one or more —

    OH, —

    OE4 or —

    NH2, or mixtures thereof;

    or E1 is a group of formula IV or V embedded imagewhereE27 and E28 are independently alkyl of 1 to 18 carbon atoms, or cycloalkyl of 5 to 12 carbon atoms;

    E22, E23, E24, E25 and E26 are independently hydrogen, halogen, straight or branched alkyl of 1 to 18 carbon atoms, alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more halogen, —

    OCOE11, —

    OE4, —

    NCO, —

    NHCOE11, or —

    NE7E8, or mixtures thereof, where E4 is straight or branched chain alkyl of 1 to 24 carbon atoms or straight or branched chain alkenyl of 2 to 18 carbon atoms;

    or said alkyl or said alkenyl interrupted by one or more —

    O—

    , —

    NH—

    or —

    NE4

    groups or mixtures thereof and which can be unsubstituted or substituted by one or more —

    OH, —

    OE4 or —

    NH2, or mixtures thereof;

    or E22, E23, E24, E25 and E26 are independently phenyl, —

    OH, —

    OCOE11, —

    OE29, —

    NCO, —

    NHCOE11 or —

    NE7E8, cyano, nitro, perfluoroalkyl of 1 to 12 carbon atoms, —

    COG3, —

    COOG3, —

    CON(G3)2, —

    CONHG3, E3S—

    , E3SO—

    , E3SO2

    , —

    P(O)(C6H5)2, —

    P(O))OG3)2, —

    SO2

    X1

    E29;

    X1 is —

    O—

    , —

    NH—

    or —

    NE4

    ;

    E29 is straight or branched chain alkyl of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, said alkyl or said alkenyl substituted by one or more —

    OH, —

    OCOE11, —

    OE4, —

    NCO, —

    NHCOE11, —

    NE7E8, phthalimido, embedded imageor mixtures thereof, where E4 is straight or branched chain alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms;

    or said alkyl or said alkenyl interrupted by one or more —

    O—

    , —

    NH—

    or —

    NE4

    groups or mixtures thereof and which can be unsubstituted or substituted by one or more —

    OH, —

    OE4 or —

    NH2, or mixtures thereof;

    or E29 is phenyl or phenylalkyl of 7 to 15 carbon atoms, or said phenyl or said phenylalkyl substituted by one to three alkyl groups of 1 to 4 carbon atoms;

    E2 is straight or branched alkyl chain of 1 to 24 carbon atoms, straight or branched chain alkenyl of 2 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, phenyl, or said phenyl or said phenylalkyl substituted on the phenyl ring by one to three alkyl of 1 to 4 carbon atoms;

    or E2 is alkyl of 1 to 24 carbon atoms or said alkenyl of 2 to 18 carbon atoms substituted by one or more —

    OH, —

    OCOE11, —

    OE4, —

    NCO, —

    NHCOE11 or —

    NE7E8, or mixtures thereof, where E4 is straight or branched chain alkyl of 1 to 24 carbon atoms or alkenyl of 2 to 18 carbon atoms;

    or said alkyl or said alkenyl interrupted by one or more —

    O—

    , —

    NH—

    or —

    NE4

    groups or mixtures thereof and which can be unsubstituted or substituted by one or more —

    OH, —

    OE4 or —

    NH2 groups or mixtures thereof, or E2 is a group of formula IV or formula V as described above;

    n is 1 or 2, when n is 1, E5 is OE6 or NE7E8, or E5 is —

    PO(OE12)2, —

    OSi(E11)3 or —

    OCO—

    E11, or straight or branched chain C1-C24alkyl which is interrupted by —

    O—

    , —

    S—

    or —

    NE11 and which can be unsubstituted or substituted by —

    OH or —

    OCO—

    E11, C5-C12 cycloalkyl which is unsubstituted or substituted by —

    OH, straight chain or branched C2-C18alkenyl which is unsubstituted or substituted by —

    OH, C7-C15aralkyl, —

    CH2

    CHOH—

    E13 or glycidyl, E6 is hydrogen, straight or branched chain C1-C24alkyl which is unsubstituted or substituted by one or more OH, OE4 or NH2 groups, or —

    OE6 is —

    (OCH2CH2)wOH or —

    (OCH2CH2)wOE21 where w is 1 to 12 and E21 is alkyl of 1 to 12 carbon atoms, E7 and E8 are independently hydrogen, alkyl of 1 to 18 carbon atoms, straight or branched chain C3-C18alkyl which is interrupted by —

    O—

    , —

    S—

    or —

    NE11

    , straight or branched chain alkenyl of 2 to 18 carbon atoms, C5-C12cycloalkyl, C6-C14aryl or C1-C3hydroxylalkyl, or E7 and E8 together with the N atom are a pyrrolidine, piperidine, piperazine or morpholine ring, or E5 is —

    X—

    (Z)p

    Y—

    E15 whereinX is —

    O—

    or —

    N(E16)—

    , Y is —

    O—

    or —

    N(E17)—

    , Z is C2-C12-alkylene, C4-C12-alkylene interrupted by one to three nitrogen atoms, oxygen atoms or a mixture thereof, or is C3-C12-alkylene, butenylene, butynylene, cyclohexylene or phenylene, each substituted by a hydroxyl group, m is zero, 1 or 2, p is 1, or p is also zero when X and Y are —

    N(E16)— and



    N(E17)—

    , respectively, E15 is a group —

    CO—

    C(E18)═

    C(H)E19 or, when Y is —

    N(E17)—

    , forms together with E17 a group —

    CO—

    CH═

    CH—

    CO—

    , wherein E18 is hydrogen or methyl, and E19 is hydrogen, methyl or —

    CO—

    X—

    E20, wherein E20 is hydrogen, C1-C12-alkyl or a group of the formula;

    embedded imagewherein the symbols E1, G2, X, Z, m and p have the meanings defined above, and E16 and E17 independently of one another are hydrogen, C1-C12-alkyl, C3-C12-alkyl interrupted by 1 to 3 oxygen atoms, or is cyclohexyl or C7-C15aralkyl, and E16 together with E17 in the case where Z is ethylene, also forms ethylene,when n is 2, E5 is one of divalent radicals —

    O—

    E9

    O—

    or —

    N(E11)—

    E10

    N(E11)—

    , E9 is C2-C8alkylene, C4-C8alkenylene, C4alkynylene, cyclohexylene, straight or branched chain C4-C10alkylene which is interrupted by —

    O—

    or by —

    CH2

    CHOH—

    CH2

    O—

    E14

    O—

    CH2

    CHOH—

    CH2

    , E10 being straight or branched chain C2-C12alkylene which may be interrupted by —

    O—

    , cyclohexylene, or embedded imageE10 and E11 with the two nitrogen atoms form a piperazine ring,E14 is straight or branched chain C2-C8alkylene, straight or branched chain C4-C10alkylene which is interrupted by —

    O—

    , cycloalkylene, arylene or embedded imageE11 is hydrogen, straight or branched chain C1-C18alkyl, C5-C12cycloalkyl, straight or branched chain C2-C18alkenyl, C6-C14 aryl or C7-C15aralkyl, E12 is straight or branched chain C1-C18alkyl, straight or branched chain C3-C18alkenyl, C5-C10cycloalkyl, C6-C16aryl or C7-C15aralkyl, E13 is hydrogen, straight chain or branched C1-C18alkyl which is substituted by —

    PO(OE12)2, phenyl which is unsubstituted or substituted by OH, C7-C15aralkyl or —

    CH2OE12, E13 is alkyl of 1 to 20 carbon atoms, hydroxyalkyl of 2 to 20 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or said aryl substituted by one or two alkyl of 1 to 4 carbon atoms or 1,1,2,2-tetrahydroperfluoroalkyl where the perfluoroalkyl moiety is of 6 to 16 carbon atoms, T is —

    SO—

    , —

    SO2

    , —

    SO—

    E—

    SO—

    , —

    SO2

    E—

    SO2

    , —

    CO—

    , —

    CO—

    CO—

    , —

    CO—

    CH2

    CO—

    , —

    CO—

    E—

    CO—

    , —

    COO—

    E—

    OCO—

    or —

    CO—

    NG5

    E—

    NG5

    CO—

    , where E is alkylene of 2 to 12 carbon atoms, cycloalkylene of 5 to 12 carbon atoms, or alkylene interrupted or terminated by cyclohexylene of 8 to 12 carbon atoms;

    G5 is G3 or hydrogen, and with the proviso that at least one of E1 and E2 must contain a group of formula IV where E22 to E26 are not each hydrogen;

    where if 1 to 4 of E22 to E26 hydrogen, the remaining E22 to E26 groups are not each alkyl of 1 to 4 carbon atoms; and

    where if 4 of E22 to E26 are each hydrogen, the remaining E22 to E26 group is not halogen.

View all claims
  • 1 Assignment
Timeline View
Assignment View
    ×
    ×