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US 4,309,529 AGranted
Water-dispersible energy curable heterocyclic group-containing polyesters
AssigneeMinnesota Mining and Manufacturing Company
InventorLarry A. Wendling
Life of this patent
Estimating the term…
Abstract
Water-dispersible radiation curable polyesters having backbone hydantoin groups and alpha-methylene groups are disclosed. These polyesters are useful in the field of graphic arts.
Claims27
A composition comprising an energy-curable polyester, said polyester being crosslinkable and having heterocyclic moieties and backbone alpha-methylene groups and repeating units of the general formula:
- ##STR9## wherein R is a single bond or an alkylene group having 1 to 6 carbon atoms and optionally one catenary oxygen;
- R.sup.1 is hydrogen, ##STR10## wherein R.sup.3 is alkenyl or alkyl having 2 to 5 carbon atoms and can be substituted by phenyl or carboxyl and R.sup.4 is aliphatic or aromatic hydrocarbyl having up to 8 carbon atoms;
- R.sup.2 is hydrogen or methyl;
- W is a divalent group that is required to complete a 5- or 6-membered heterocyclic ring, wherein W is ##STR11## and wherein R.sup.5, R.sup.6, R.sup.7, and R.sup.8 are independently hydrogen or lower alkyl or 1 to 4 carbon atoms;
- Q is the divalent or trivalent residue of hydrocarbyl di- or tri-carboxylic acids, said residue formed by the removal of active hydrogens from the carboxylic acid groups and containing up to 40 carbon atoms and optionally containing catenary oxygen atoms;
- and
- a is zero or one, but can be one for no more than 20 mole percent of the carboxylic acids, and ##STR12##
4 more elements
The method of preparing an energy-curable polyester, said polyester being crosslinkable and having heterocyclic moieties and backbone alpha-methylene groups and having repeating units of the general formula:
- ##STR14## wherein R is a single bond or an alkylene group having 1 to 6 carbon atoms and optionally one catenary oxygen;
- R.sup.1 is hydrogen, ##STR15## wherein R.sup.3 is alkenyl or alkyl having 2 to 5 carbon atoms and can be substituted by phenyl or carboxyl and R.sup.4 is aliphatic or aromatic hydrocarbyl having up to 8 carbon atoms;
- R.sup.2 is hydrogen or methyl;
- W is a divalent group that is required to complete a 5- or 6-membered heterocyclic ring, wherein W is ##STR16## and wherein R.sup.5, R.sup.6, R.sup.7, and R.sup.8 are independently hydrogen or lower alkyl of 1 to 4 carbon atoms;
- Q is the divalent or trivalent residue of hydrocarbyl di- or tri-carboxylic acids, said residue formed by the removal of active hydrogens from the carboxylic acid groups and containing up to 40 carbon atoms and optionally containing catenary oxygen atoms;
- and
- a is zero or one, but can be one for no more than 20 mole percent of the dicarboxylic acids, and ##STR17## which method includes the steps of (a) admixing together
- (1) 1.0 mole equivalent of a bis-(epoxy)heterocyclic compound having the formula:
- ##STR18## wherein R, R.sup.2 and W are as defined above;
- (2) 0.8 to 1.2 mole equivalents of a polycarboxylic acid having the formula:
- ##STR19## wherein Q and a are as defined above;
- (3) a catalytically active amount of a base polymerization catalyst
- (4) less than 200 ppm by weight of a thermal polymerization inhibitor,
- (b) reacting components (1) and (2).
11 more elements
Dependencies are inferred from the claim text.