US 5,149,806 AGranted

Azlactone Michael adducts

AssigneeMinnesota Mining and Manufacturing Company

InventorsDean M. Moren, Steven M. Heilmann, Larry R. Krepski, Jerald K. Rasmussen

Life of this patent

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Abstract

Azlactone-functional Michael adducts are disclosed which are the Michael reaction products of 2-alkenyl azlactones and Michael donors selected from carbon and nitrogen nucleophiles. Reaction products which contain a plurality of azlactone groups are useful as step growth monomers in adhesives, sealants, and coatings.

Claims13

Dependent claims

An azlactone-functional adduct having the formula ##STR95## wherein p.sup.1 and p.sup.2 independently have integral values of 1 to (the valence of X.sup.1 or X.sup.2) -1, where p.sup.1 relates to X.sup.1 and p.sup.2 to X.sup.2 ;

R.sup.1, R.sup.2, R.sup.7, and R.sup.8 independently represent an alkyl group, a cycloalkyl group, an aryl group, or at least one of (R.sup.1 and R.sup.2) and (R.sup.7 and R.sup.8) taken together with the carbon atom to which they are joined form a ring of 4 to 12 atoms;
R.sup.3, R.sup.4, R.sup.9, and R.sup.10 are independently hydrogen or lower alkyl;
R.sup.5 and R.sup.6 independently are hydrogen or methyl;
n.sup.1 and n.sup.2 independently are 0 or 1;
X.sup.1 and X.sup.2 independently are selected from the group consisting of --CH.sub.2 (when at least one of p.sup.1 and p.sup.2 =1);
--CH (when at least one of p.sup.1 and p.sup.2 =2);
--C (when at least one of p.sup.1 and p.sup.2 =3);
--CR.sup.11 R.sup.12 in which R.sup.11 and R.sup.12 are selected from the group consisting of alkyl, alkenyl, cycloalkyl, and aryl monovalent groups, a single bond, and polyvalent alkylene, alkenylene, cycloalkylene, or arylene linking groups;
--CHR.sup.11 ;
--CR.sup.11 ;
--CW.sup.1 W.sup.2 in which W.sup.1 and W.sup.2 are independently selected from R.sup.11 O.sub.2 C--, R.sup.11 (CO)--, N.tbd.C--, R.sub.F (CO)-- in which R.sub.F is a substantially perfluorinated alkyl, cycloalkyl, or aryl group, R.sup.11 NH(CO)--, R.sup.11 R.sup.12 N(CO)--, R.sup.11 SO.sub.2 --, R.sup.11 R.sup.12 C.dbd.N--, R.sup.11 N.dbd.(R.sup.12)C--, R.sup.11 (CS)--, R.sup. 11 S.sub.2 C--, R.sup.11 NH(CS)--, R.sup.11 R.sup.12 N(CS)--, R.sup.11 R.sup.12 C.dbd.CR.sup.13 -- in which R.sup.13 is defined the same as R.sup.11 and R.sup.12, and O.sub.2 N-- groups;
--CR.sup.11 W.sup.1 ;
--CHW.sup.1 ;
--CW.sup.1 ;
--NR.sup.14 in which R.sup.14 (linking at least one of X.sup.1 to Y.sup.1, X.sup.1 to G, X.sup.1 to X.sup.2, X.sup.2 to Y.sup.2, and X.sup.2 to G) is a single bond, alkylene, alkenylene, or arylene group such that the ring formed contains 4 to 6 ring atoms;
and --NW.sup.1 ;
Z.sup.1 and Z.sup.2 independently are C, N, or S.dbd.O;
Y.sup.1 and Y.sup.2 independently are doubly bonded oxygen (.dbd.O);
doubly bonded sulfur (.dbd.S);
.dbd.CR.sup.15 R.sup.16, or --CR.sup.15 .dbd.CR.sup.16 R.sup.17 in which R.sup.15 and R.sup.16 independently are defined the same as R.sup.11, R.sup.12, and R.sup.13, except that R.sup.15 can be an electron pair, and in which R.sup.17 is a monovalent group selected from alkyl, alkenyl, cycloalkyl, and aryl groups;
.dbd.NR.sup.15 (to include triply bonded nitrogen (.tbd.N:) when R.sup.15 is an electron pair and G is a single bond from at least one of Y.sup.1 to Z.sup.1 and Y.sup.2 to Z.sup.2);
or --NR.sup.18 R.sup.19 in which R.sup.18 and R.sup.19 independently can be hydrogen, alkyl, cycloalkyl, aryl, a single bond, alkylene, cycloalkylene, or arylene, or together with the nitrogen atom to which they are joined form a ring of 4 to 12 ring atoms;
and
G is --H;
--NR.sup.20 R.sup.21 in which R.sup.20 and R.sup.21 independently are defined the same as R.sup.11, R.sup.12, and R.sup.13 ;
--NHR.sup.20 ;
--R.sup.20 ;
or --OR.sup.20 ;
.dbd.O;
polymeric monovalent and polyvalent groups;
an electron pair;
or a single bond;
and
q is an integer of zero or greater and is equal to (the valence of G)-1;
wherein said azlactone-functional adduct is prepared by a process comprising the step of reacting at least one 2-alkenyl azlactone Michael acceptor of Formulae VIIa and VIIb:
##STR96## wherein:
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, n.sup.1, n.sup.2, p.sup.1, and p.sup.2 are as previously defined,
with a Michael donor of Formula VIII ##STR97## wherein X.sup.1, X.sup.2, Y.sup.1, Y.sup.2, Z.sup.1, Z.sup.2, G, q, p.sup.1 and p.sup.2 are as previously defined, to provide said azlactone-functional adduct.

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An azlactone-functional adduct having the formula ##STR98## wherein p.sup.1 and p.sup.2 independently have integral values of 1 to (the valence of X.sup.1 or X.sup.2) -1, where p.sup.1 relates to X.sup.1 and p.sup.2 to X.sup.2 ;

R.sup.1, R.sup.2, R.sup.7, and R.sup.8 independently represent an alkyl group, a cycloalkyl group, an aryl group, or at least one of (R.sup.1 and R.sup.2) and (R.sup.7 and R.sup.8) taken together with the carbon atom to which they are joined form a ring of 4 to 12 atoms;
R.sup.3, R.sup.4, R.sup.9, and R.sup.10 are independently hydrogen or lower alkyl;
R.sup.5 and R.sup.6 independently are hydrogen or methyl;
n.sup.1 and n.sup.2 independently are 0 or 1;
X.sup.1 and X.sup.2 independently are selected from the group consisting of --CH.sub.2 (when at least one of p.sup.1 and p.sup.2 =1);
--CH (when at least one of p.sup.1 and p.sup.2 =2);
--C (when at least one of p.sup.1 and p.sup.2 =3);
--CR.sup.11 R.sup.12 in which R.sup.11 and R.sup.12 are selected from the group consisting of alkyl, alkenyl cycloalkyl, and aryl monovalent groups;
a single bond;
and polyvalent alkylene, alkenylene, cycloalkylene, or arylene linking groups;
--CHR.sup.11 ;
--CR.sup.11 ;
--CW.sup.1 W.sup.2 in which W.sup.1 and W.sup.2 are independently selected from R.sup.11 O.sub.2 C--, R.sup.11 (CO)--, N.tbd.C--, R.sub.F (CO)-- in which R.sub.F is a substantially perfluorinated alkyl, cycloalkyl, or aryl group, R.sup.11 NH(CO)--, R.sup.11 R.sup.12 N(CO)--, R.sup.11 SO.sub.2 --, R.sup.11 R.sup.12 C.dbd.N--, R.sup.11 N.dbd.(R.sup.12)C--, R.sup.11 ( CS)--, R.sup.11 S.sub.2 C--, R.sup.11 NJ(CS)--, R.sup.11 R.sup.12 N(CS)--, R.sup.11 R.sup.12 C.dbd.CR.sup.13 -- in which R.sup.13 is defined the same as R.sup.11 and R.sup.12, and O.sub.2 N-- groups;
--CR.sup.11 W.sup.1 ;
--CHW.sup.1 ;
--CW.sup.1 ;
--NR.sup.14 in which R.sup.14 (linking at least one of X.sup.1 to Y.sup.1, X.sup.1 to G, X.sup.1 to X.sup.2, X.sup.2 to Y.sup.2, and X.sup.2 to G) is a single bond, alkylene, alkenylene, or arylene group such that the ring formed contains 4 to 6 ring atoms;
and --NW.sup.1 ;
Z.sup.1 and Z.sup.2 independently are C;
Y.sup.1 and Y.sup.2 independently are doubly bonded oxygen (.dbd.O) doubly bonded sulfur (.dbd.S);
.dbd.CR.sup.15 R.sup.16, or --CR.sup.15 .dbd.CR.sup.16 R.sup.17 in which R.sup.15 and R.sup.16 independently are defined the same as R.sup.11, R.sup.12, and R.sup.13, except that R.sup.15 can be an electron pair, and in which R.sup.17 is a monovalent group selected from alkyl, alkenyl, cycloalkyl, and aryl groups;
.dbd.NR.sup.15 (to include triply bonded nitrogen (.tbd.N:) when R.sup.15 is an electron pair and G is a single bond from at least one of Y.sup.1 to Z.sup.1 and Y.sup.2 to Z.sup.2);
or --NR.sup.18 R.sup.19 in which R.sup.18 and R.sup.19 independently can be hydrogen, alkyl, cycloalkyl, aryl, a single bond, alkylene, cycloalkylene, or arylene, or together with the nitrogen atom to which they are joined form a ring of 4 to 12 ring atoms;
G is --H;
--NR.sup.20 R.sup.21 in which R.sup.20 and R.sup.21 independently are defined the same as R.sup.11, R.sup.12, and R.sup.13 ;
--NHR.sup.20 ;
--R.sup.20 ;
or --OR.sup.20 ;
.dbd.O;
polymeric monovalent and polyvalent groups;
an electron pair;
or a single bond;
and
q is an integer of 0 or greater and is equal to (the valence of G)-1.

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Dependencies are inferred from the claim text.

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Abstract

R.sup.1, R.sup.2, R.sup.7, and R.sup.8 independently represent an alkyl group, a cycloalkyl group, an aryl group, or at least one of (R.sup.1 and R.sup.2) and (R.sup.7 and R.sup.8) taken together with the carbon atom to which they are joined form a ring of 4 to 12 atoms;
R.sup.3, R.sup.4, R.sup.9, and R.sup.10 are independently hydrogen or lower alkyl;
R.sup.5 and R.sup.6 independently are hydrogen or methyl;
n.sup.1 and n.sup.2 independently are 0 or 1;
X.sup.1 and X.sup.2 independently are selected from the group consisting of --CH.sub.2 (when at least one of p.sup.1 and p.sup.2 =1);
--CH (when at least one of p.sup.1 and p.sup.2 =2);
--C (when at least one of p.sup.1 and p.sup.2 =3);
--CR.sup.11 R.sup.12 in which R.sup.11 and R.sup.12 are selected from the group consisting of alkyl, alkenyl, cycloalkyl, and aryl monovalent groups, a single bond, and polyvalent alkylene, alkenylene, cycloalkylene, or arylene linking groups;
--CHR.sup.11 ;
--CR.sup.11 ;
--CW.sup.1 W.sup.2 in which W.sup.1 and W.sup.2 are independently selected from R.sup.11 O.sub.2 C--, R.sup.11 (CO)--, N.tbd.C--, R.sub.F (CO)-- in which R.sub.F is a substantially perfluorinated alkyl, cycloalkyl, or aryl group, R.sup.11 NH(CO)--, R.sup.11 R.sup.12 N(CO)--, R.sup.11 SO.sub.2 --, R.sup.11 R.sup.12 C.dbd.N--, R.sup.11 N.dbd.(R.sup.12)C--, R.sup.11 (CS)--, R.sup. 11 S.sub.2 C--, R.sup.11 NH(CS)--, R.sup.11 R.sup.12 N(CS)--, R.sup.11 R.sup.12 C.dbd.CR.sup.13 -- in which R.sup.13 is defined the same as R.sup.11 and R.sup.12, and O.sub.2 N-- groups;
--CR.sup.11 W.sup.1 ;
--CHW.sup.1 ;
--CW.sup.1 ;
--NR.sup.14 in which R.sup.14 (linking at least one of X.sup.1 to Y.sup.1, X.sup.1 to G, X.sup.1 to X.sup.2, X.sup.2 to Y.sup.2, and X.sup.2 to G) is a single bond, alkylene, alkenylene, or arylene group such that the ring formed contains 4 to 6 ring atoms;
and --NW.sup.1 ;
Z.sup.1 and Z.sup.2 independently are C, N, or S.dbd.O;
Y.sup.1 and Y.sup.2 independently are doubly bonded oxygen (.dbd.O);
doubly bonded sulfur (.dbd.S);
.dbd.CR.sup.15 R.sup.16, or --CR.sup.15 .dbd.CR.sup.16 R.sup.17 in which R.sup.15 and R.sup.16 independently are defined the same as R.sup.11, R.sup.12, and R.sup.13, except that R.sup.15 can be an electron pair, and in which R.sup.17 is a monovalent group selected from alkyl, alkenyl, cycloalkyl, and aryl groups;
.dbd.NR.sup.15 (to include triply bonded nitrogen (.tbd.N:) when R.sup.15 is an electron pair and G is a single bond from at least one of Y.sup.1 to Z.sup.1 and Y.sup.2 to Z.sup.2);
or --NR.sup.18 R.sup.19 in which R.sup.18 and R.sup.19 independently can be hydrogen, alkyl, cycloalkyl, aryl, a single bond, alkylene, cycloalkylene, or arylene, or together with the nitrogen atom to which they are joined form a ring of 4 to 12 ring atoms;
and
G is --H;
--NR.sup.20 R.sup.21 in which R.sup.20 and R.sup.21 independently are defined the same as R.sup.11, R.sup.12, and R.sup.13 ;
--NHR.sup.20 ;
--R.sup.20 ;
or --OR.sup.20 ;
.dbd.O;
polymeric monovalent and polyvalent groups;
an electron pair;
or a single bond;
and
q is an integer of zero or greater and is equal to (the valence of G)-1;
wherein said azlactone-functional adduct is prepared by a process comprising the step of reacting at least one 2-alkenyl azlactone Michael acceptor of Formulae VIIa and VIIb:
##STR96## wherein:
R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9, R.sup.10, n.sup.1, n.sup.2, p.sup.1, and p.sup.2 are as previously defined,
with a Michael donor of Formula VIII ##STR97## wherein X.sup.1, X.sup.2, Y.sup.1, Y.sup.2, Z.sup.1, Z.sup.2, G, q, p.sup.1 and p.sup.2 are as previously defined, to provide said azlactone-functional adduct.

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