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Stabilization of acid catalyzed thermoset resins

  • US 5,112,890 A
  • Filed: 10/19/1988
  • Issued: 05/12/1992
  • Est. Priority Date: 09/21/1987
  • Status: Expired due to Term
First Claim
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1. A stabilized stoving lacquer composition comprising(a) an acid catalyzed thermoset resin based on hot crosslinkable acrylic, polyester, polyurethane, polyamide or alkyd resins, and(b) an effective oxidative and light stabilizing amount of a hindered amine derivative corresponding to the formulae A-P ##STR16## wherein R is hydrogen or methyl,R1 is independently C1 -C18 alkyl, C2 -C18 alkenyl, C2 -C18 alkynyl, C5 -C12 cycloalkyl, C6 -C10 bicycloalkyl, C5 -C8 cycloalkenyl C6 -C10 aryl, C7 -C9 aralkyl, C7 -C9 aralkyl substituted by alkyl or aryl, or ##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 hydrogen, C1 -C18 alkyl optionally interrupted by one or more oxygen atoms, C2 -C12 alkenyl, C6 -C10 aryl, C7 -C18 aralkyl glycidyl, a monovalent acyl radical of an aliphatic, cycloaliphatic, araliphatic or aromatic carboxylic acid, or of a carbamic acid, or ##STR18## wherein x is 0 or 1, or ##STR19## wherein y is 2-4;

    when m is 2,R2 is C1 -C12 alkylene, C4 -C12 alkenylene, xylylene, a divalent acyl radical of an aliphatic, cycloaliphatic, araliphatic or aromatic dicarboxylic acid or of a dicarbamic acid;

    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 ##STR20## or R3 and R4 together when p is 1 can be alkylene of 4 to 65 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--O--CH2 --CH(OH)--CH2 -- wherein X is C2 -C10 alkylene, C6 -C15 arylene or Chd 6-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 ##STR21## 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,n is 1 or 2,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 hydroxylakylene or C4 -C22 acyloxyalkylene;

    when n is 2,R5 and R'"'"'5 together are (--CH2)2 C(CH2 --)3 ;

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

    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)t --COO--Q or of the formula --(CH2)t --O--CO--Q wherein t 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 CHY(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, the 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 ##STR22## or a group of the formula ##STR23## wherein G1 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 ##STR24## T12 is piperazinyl, ##STR25## wherein R11 is the same as R3 or is also ##STR26## a, b and c are independently 2 or 3, and f is 0 or 1;

    e is 2, 3 or 4;

    T13 is the same as R2 with the proviso that T13 cannot be hydrogen when n 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, naphtyl, said phenyl or said naphthyl 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 a previously defined when m is 1;

    G 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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