O-carbonyl N-hydroxy hindered amine stabilizers

  • US 5,300,647 A
  • Filed: 05/28/1993
  • Issued: 04/05/1994
  • Est. Priority Date: 09/21/1987
  • Status: Expired due to Fees
First Claim
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1. A compound corresponding to the formulae ##STR16## wherein R is hydrogen or methyl,R1 is ##STR17## wherein D is C1 -C18 alkyl, C1 -C18 alkoxy, phenyl, phenyl substituted by hydroxy, alkyl or alkoxy, or amino or amino mono- or disubstituted by alkyl or phenyl;

  • m is 1-4,when m is 1,R2 is ##STR18## wherein x is 0 or 1, or ##STR19## wherein y is 2-4;

    when m is 2 and D is alkyl, phenyl or substituted phenyl,R2 is C1 -C12 alkylene, C4 -C12 alkenylene, xylylene, a divalent acyl radical or a cycloaliphatic, araliphatic or aromatic dicarboxylic acid or of a dicarbamic acid, ##STR20## wherein D1 is an aryl, aralkyl or 3,5-di-t-butyl-4-hydroxybenzyl radical, D2 is D1 or hydrogen, D3 is an alkenyl radical containing up to 18 carbon atoms, and d is 0-20;

    when m is 2 and D is amino, substituted amino or alkoxy,R2 is C1 -C12 alkenylene, xylylene, a divalent acyl radical of an aliphatic, cycloaliphatic, araliphatic or aromatic dicarboxylic acid or of a dicarbamic acid;

    ##STR21## wherein D4 and D5 are independently hydrogen, an alkyl radical containing up to 8 carbon atoms, an aryl, aralkyl or 3,5-di-t-butyl-4-hydroxybenzyl radical, D6 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;

    p is 1, 2 or 3,R3 is hydrogen, C1 -C12 alkyl, C5 -C7 cycloalkyl, C7 -C9 aralkyl, C2 -C18 alkanoyl, C3 -C5 alkenoyl or benzoyl;

    when p is 1,R4 is hydrogen, C1 -C18 alkyl, C5 -C7 cycloalkyl, C2 -C8 alkenyl unsubstituted or substituted by a cyano, carbonyl or carbamide group, aryl, aralkyl, or it is glycidyl, a group of the formula --CH2 --CH(OH)--Z or of the formula --CO--Z-- or --CONH--Z wherein Z is hydrogen, methyl or phenyl;

    or a group of the formulae ##STR22## or R3 and R4 together with p is 1 can be alkylene of 4 to 6 carbon atoms or 2-oxopolyalkylene or the cyclic acyl radical of an aliphatic or aromatic 1,2- or 1,3-dicarboxylic acid,when p is 2,R4 is a direct bond or is C1 -C12 alkylene, C6 -C12 arylene, xylylene, a --CH2 CH(OH)--CH2 group, or a group --CH2 --CH(OH)--CH2 --O--X--X--O--CH2 --CH(OH)--CH2 -- wherein X is C2 -C10 alkylene, C6 -C15 arylene or C6 -C12 cycloalkylene;

    or, provided that R3 is not alkanoyl, alkenoyl or benzoyl, R4 can also be a divalent acyl radical of an aliphatic, cycloaliphatic or aromatic dicarboxylic acid or dicarbamic acid, or can be the group --CO--;

    orR4 is ##STR23## where T8 and T9 are independently hydrogen, alkyl of 1 to 18 carbon atoms, or T8 and T9 together are alkylene of 4 to 6 carbon atoms or 3-oxapentamethylene,when p is 3,R4 is 2,4,6-triazinyl,when n is 1,R5 and R'"'"'5 are independently C1 -C12 alkyl, C2 -C12 alkenyl, C7 -C12 aralkyl, or R5 is also hydrogen, or R5 and R'"'"'5 together are C2 -C8 alkylene or hydroxyalkylene or C4 -C22 acyloxyalkylene;

    when n is 2,R5 and R'"'"'5 together are (--CH2)2 C(CH2 --)2 ;

    R6 is hydrogen, C1 -C12 alkyl, allyl, benzyl, glycidyl or C2 -C6 alkoxyalkyl;

    when n is 1,R7 is hydrogen, C1 -C12 alkyl, C3 -C5 alkenyl, C7 -C9 aralkyl, C5 -C7 cycloalkyl, C2 -C4 hydroxyalkyl, C2 -C6 alkoxyalkyl, C6 -C10 aryl, glycidyl, a group of the formula --(CH2)m --COO--Q or of the formula --(CH2)m --O--CO--Q wherein m is 1 or 2, and Q is C1 -C4 alkyl or phenyl;

    orwhen n is 2,R7 is C2 -C12 alkylene, C6 -C12 arylene, a group --CH2 CH(OH)--CH2 --O--X--O--CH2 --CH(OH)--CH2 -- wherein X is C2 -C10 alkylene, C6 -C15 arylene or C6 -C12 cycloalkylene, or a group --CH2 CH(OZ'"'"')CH2 --(OCH2 --CH(OZ'"'"')CH2)2 -- wherein Z'"'"' is hydrogen, C1 -C18 alkyl, allyl, benzyl, C2 -C12 alkanoyl or benzoyl;

    Q1 is --N(R8)-- or --O--;

    E is C1 -C3 alkylene, he group --CH2 --CH(R9)--O-- wherein R9 is hydrogen, methyl or phenyl the group --(CH2)3 --NH-- or a direct bond;

    R10 is hydrogen or C1 -C18 alkyl;

    R8 is hydrogen, C1 -C18 alkyl, C5 -C7 cycloalkyl, C7 -C12 aralkyl, cyanoethyl, C6 -C10 aryl, the group --CH2 --CH(R9)--OH wherein R9 has the meaning defined above;

    a group of the formula ##STR24## or a group of the formula ##STR25## wherein G can be C2 -C6 alkylene or C6 -C12 arylene;

    or R8 is a group --E--CO--NH--CH2 --OR10 ;

    T3 is ethylene or 1,2-propylene, or is the repeating structural unit derived from an alpha-olefin copolymer with an alkyl acrylate or methacrylate;

    k is 2 to 100;

    T4 has the same meaning as R4 when p is 1 or 2,T5 is methyl,T6 is methyl or ethyl, or T5 and T6 together are tetramethylene or pentamethylene,M and Y are independently methylene or carbonyl;

    T7 is the same as R7,T10 and T11 are independently alkylene of 2 to 12 carbon atoms, or T11 is ##STR26## T12 is piperazinyl, ##STR27## where R11 is the same as R3 or is also ##STR28## a, b and c are independently 2 or 3, and f is 0 or 1, e is 3 or 4,T13 is the same as R4 with the proviso that T13 cannot be hydrogen when p is 1;

    E1 and E2, being different, each are --CO-- or N(E5)-- wherein E5 is hydrogen, C1 -C12 alkyl or C4 -C22 alkoxycarbonylalkyl;

    E3 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl, said phenyl or said napthyl substituted by chlorine or by alkyl of 1 to 4 carbon atoms, or phenylalkyl of 7 to 12 carbon atoms, or said phenylalkyl substituted by alkyl of 1 to 4 carbon atoms;

    E4 is hydrogen, alkyl of 1 to 30 carbon atoms, phenyl, naphthyl or phenylalkyl of 7 to 12 carbon atoms, orE3 and E4 together are polymethylene of 4 to 17 carbon atoms, or said polymethylene substituted by up to four alkyl groups of 1 to 4 carbon atoms;

    R2 of formula (N) is as previously defined when m is 1;

    G2 is a direct bond, C1 -C12 alkylene, phenylene or --NH--G'"'"'--NH wherein G'"'"' is C1 -C12 alkylene; and

    E6 is an aliphatic or aromatic tetravalent radical.

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