Randomly terminated capped polymers
AssigneeMillmaster Onyx Corporation
InventorsHarold A. Green, John J. Merianos, Alfonso N. Petrocci
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Abstract
Anti-microbial polymeric quaternary ammonium compounds having linear chains which terminate in quaternary ammonium moieties, such compounds being formed by polymerization which is carried out in such a manner that the linear chains thereof are terminated in random fashion, the reaction resulting in the formation of the compounds being a one-step reaction between 1,4-dihalo-2-butene and a mixture of a difunctional tertiary amine and a monofunctional tertiary amine wherein the molar quantity of the difunctional amine is greater than the molar quantity of the monofunctional amine.
Claims6
A product formed by a one-step reaction between 1,4-dihalo-2-butene and a mixture of a difunctional tertiary amine with a monofunctional tertiary amine, the molar ratio of the difunctional amine to the monofunctional amine being from about 2:1 to 30:1, the number of moles of the 1,4-dihalo-2-butene being about equal to the sum of the number of moles of the difunctional tertiary amine plus one-half the number of moles of the monofunctional amine, the reaction being effected at a temperature of between about 50.degree.-70.degree. C. and during a time interval of between about 1 to 10 hours, the difunctional tertiary amime having the formula:
- ##STR3## wherein Z represents either (1) a divalent aliphatic radical of from 2 to 10 carbon atoms containing from 0 to 2 hydroxyl substituents and from 0 to 2 ethylenic double bonds, and R.sup.I and R.sup.II may either be (A) the same or different and may be either (a) an alkyl group of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has one alkyl substituent of from 2 to 20 carbon atoms, or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents;
- (B) R.sup.I and R.sup.II, taken together with N, form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms;
- or (C) R.sup.I and R.sup.II, taken together with N, and combined with an oxygen atom, form a N-morpholino group;
- or (2) Z represents two divalent ethylene radicals, in which case R.sup.II is absent and R.sup.I represents (a) an aliphatic radical of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has an alkyl substituent of from 2 to 20 carbon atoms;
- or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents;
- or (3) Z represents three divalent ethylene radicals in which case R.sup.I and R.sup.II are both absent;
- and the monotertiary amine having the formula:
- ##STR4## where (1) R.sup.III is an aliphatic radical of from 1 to 20 carbon atoms, having from 0 to 2 hydroxyl substituents, and R.sup.IV and R.sup.V may either be (a) the same or different and represent an aliphatic radical having from 1 to 4 carbon atoms with from 0 to 1 hydroxyl substituents, (b) taken together with N to form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms;
- (c) taken together with N, and combined with an oxygen atom to form a N-morpholino group;
- or where (2) R.sup.III, R.sup.IV, R.sup.V and N, taken together, represent quinoline, isoquinoline or hexamethylene tetramine.
A method of controlling the proliferation of deleterious microorganisms which comprises applying to said microorganisms an amount sufficient to inhibit their proliferation of a product formed by a one-step reaction between 1,4-di-halo-2-butene and a mixture of a difunctional tertiary amine with a monofunctional tertiary amine, the molar ratio of the difunctional amine to the monofunctional amine being from about 2:1 to about 30:1, the number of moles of the 1,4-di-halo-2-butene being about equal to the sum of the number of moles of the difunctional tertiary amine plus one-half the number of moles of the monofunctional amine, the reaction being effected at a temperature of between about 50.degree.-70.degree. C and during a time interval of between about 1 to 10 hours;
- the difunctional tertiary amine having the formula:
- ##STR5## wherein Z represents either (1) a divalent aliphatic radical of from 2 to 10 carbon atoms containing from 0 to 2 hydroxyl substituents and from 0 to 2 ethylenic double bonds, and R.sup.I and R.sup.II may either be (A) the same or different and may be either (a) an alkyl group of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has one alkyl substituent of from 2 to 20 carbon atoms or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents;
- (B) R.sup.I and R.sup.II, taken together with N, form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms;
- or (C) R.sup.I and R.sup.II, taken together with N, and combined with an oxygen atom, form a N-morpholino group;
- or (2) Z represents two divalent ethylene radicals, in which case R.sup.II is absent and R.sup.I represents (a) an aliphatic radical of from 1 to 20 carbon atoms having from 0 to 2 hydroxyl substituents, (b) benzyl, (c) benzyl in which the benzene moiety has an alkyl substituent of from 2 to 20 carbon atoms;
- or (d) benzyl in which the benzene moiety has from 1 to 5 methyl substituents;
- or (3) Z represents three divalent ethylene radicals in which case R.sup.I and R.sup.II are both absent;
- the monotertiary amine having the formula:
- ##STR6## where (1) R.sup.III is an aliphatic radical of from 1 to 20 carbon atoms, having from 0 to 2 hydroxyl substituents, and R.sup.IV and R.sup.V may be either (a) the same or different and represent an aliphatic radical having from 1 to 4 carbon atoms with from 0 to 1 hydroxyl substituents;
- (b) taken together with N to form a saturated or unsaturated heterocyclic ring of from 5 to 7 atoms;
- (c) taken together with N, and combined with an oxygen atom to form a N-morpholino group;
- or where (2) R.sup.III, R.sup.IV, R.sup.V and N, taken together, represent quinoline, isoquinoline or hexamethylene tetramine.
Dependencies are inferred from the claim text.