Moisture curable polyurethane hot melt adhesive composition having low levels of diisocyanate monomer
A moisture curable polyurethane hot melt adhesive composition and a process for making the same are disclosed. The moisture curable polyurethane hot melt adhesive composition includes an isocyanate-terminated polyurethane prepolymer that is the reaction product of a diisocyanate monomer component that includes at least 20% by weight asymmetrical diisocyanate monomer based on the weight of the diisocyanate monomer component and symmetrical diisocyanate monomer, at least one polyol having a number average molecular weight greater than 1000 g/mole, a monofunctional compound that includes one isocyanate-reactive group and has a molecular weight no greater than 400 g/mole, and a multifunctional compound that includes at least two isocyanate-reactive groups and has a molecular weight no greater than 400 g/mole.
1. A moisture curable hot melt adhesive composition comprising:
an isocyanate-terminated polyurethane prepolymer comprising the reaction product of
a diisocyanate monomer component comprising from 30% by weight to 65% by weight diphenylmethane-2,4′-diisocyanate monomer based on the weight of the diisocyanate monomer component, and at least 10% by weight diphenylmethane-4,4′-diisocyanate monomer based on the weight of the diisocyanate monomer component,
at least one polyol having a number average molecular weight greater than 1000 g/mole,
a monofunctional compound comprising one isocyanate-reactive group and having a molecular weight no greater than 400 g/mole, and
a multifunctional compound comprising at least two isocyanate-reactive groups and having a molecular weight no greater than 400 g/mole,
the moisture curable hot melt adhesive composition comprising no greater than 0.1% by weight diisocyanate monomer.
2. The moisture curable hot melt adhesive composition of claim 1 , wherein the stoichiometric ratio of isocyanate groups to the sum of the hydroxyl groups present on the polyol, the isocyanate-reactive group of the monofunctional compound and the isocyanate-reactive groups of the multifunctional compound is from 1.15:1 to 1.35:1.
3. The moisture curable hot melt adhesive composition of claim 1 , wherein the ratio of the weight of the monofunctional compound to the weight of the multifunctional compound is less than 0.5:1.
4. The moisture curable hot melt adhesive composition of claim 1 , wherein the ratio of the weight of the monofunctional compound to the weight of the multifunctional compound is less than 0.49:1.
5. The moisture curable hot melt adhesive composition of claim 1 further comprising a thermoplastic polymer.
6. The moisture curable hot melt adhesive composition of claim 1 further comprising a multifunctional crosslinking agent.
7. A process for preparing a moisture curable polyurethane hot melt adhesive composition, the process comprising:
reacting
at least one polyol having a number average molecular weight greater than 1000 g/mole,
a monofunctional compound comprising one isocyanate-reactive group and having a molecular weight no greater than 400 g/mole,
a multifunctional compound comprising at least two isocyanate-reactive groups and having a molecular weight no greater than 400 g/mole, and
diisocyanate monomer component comprising
at least 20% by weight asymmetrical diisocyanate monomer based on the weight of the diisocyanate monomer component, and
symmetrical diisocyanate monomer,
to form an isocyanate-terminated polyurethane prepolymer,
the moisture curable hot melt adhesive composition comprising no greater than 0.1% by weight diisocyanate monomer.
8. The process of claim 7 , wherein the process comprises a first stage and a second stage,
the first stage comprising the reacting, and
the second stage comprising adding a multifunctional crosslinking agent, a catalyst, or a combination thereof to the isocyanate-terminated polyurethane prepolymer.
9. The process of claim 7 further comprising adding a thermoplastic polymer to the composition.
10. The process of claim 7 , wherein the diisocyanate monomer component comprises at least 20% by weight diphenylmethane-2,4′-diisocyanate.
11. The process of claim 7 , wherein the diisocyanate monomer component comprises from 30% by weight to 65% by weight asymmetrical diisocyanate monomer based on the weight of the diisocyanate monomer component.
12. A moisture curable hot melt adhesive composition comprising:
an isocyanate-terminated polyurethane prepolymer comprising the reaction product of
a diisocyanate monomer component comprising
from 30% by weight to 65% by weight asymmetrical diisocyanate monomer based on the weight of the diisocyanate monomer component, and
a symmetrical diisocyanate monomer,
at least one polyol having a number average molecular weight greater than 1000 g/mole,
a monofunctional compound comprising one isocyanate-reactive group and having a molecular weight no greater than 400 g/mole, and
a multifunctional compound comprising at least two isocyanate-reactive groups and having a molecular weight no greater than 400 g/mole,
the moisture curable hot melt adhesive composition comprising no greater than 0.1% by weight diisocyanate monomer.
13. The moisture curable hot melt adhesive composition of claim 12 , wherein the stoichiometric ratio of isocyanate groups to the sum of the hydroxyl groups present on the polyol, the isocyanate-reactive group of the monofunctional compound and the isocyanate-reactive groups of the multifunctional compound being from 1.15:1 to 1.35:1.
14. The moisture curable hot melt adhesive composition of claim 12 , wherein the ratio of the weight of the monofunctional compound to the weight of the multifunctional compound is less than 0.5:1.
15. The moisture curable hot melt adhesive composition of claim 12 , wherein the ratio of the weight of the monofunctional compound to the weight of the multifunctional compound is less than 0.49:1.
16. The moisture curable hot melt adhesive composition of claim 12 further comprising a thermoplastic polymer.
17. The moisture curable hot melt adhesive composition of claim 12 further comprising a multifunctional crosslinking agent.
18. A moisture curable hot melt adhesive composition comprising:
an isocyanate-terminated polyurethane prepolymer comprising the reaction product of
a diisocyanate monomer component comprising
from 30% by weight to 65% by weight asymmetrical diisocyanate monomer based on the weight of the diisocyanate monomer component, and
a symmetrical diisocyanate monomer,
at least one polyol having a number average molecular weight greater than 1000 g/mole,
a monofunctional compound comprising one isocyanate-reactive group and having a molecular weight no greater than 400 g/mole, and
a multifunctional compound comprising at least two isocyanate-reactive groups and having a molecular weight no greater than 400 g/mole,
the ratio of the weight of the monofunctional compound to the weight of the multifunctional compound being less than 0.5:1, and
the sum of the monofunctional compound and the multifunctional compound being from 0.1% by weight to 10% by weight based on the weight of the moisture curable hot melt adhesive composition,
the stoichiometric ratio of isocyanate groups to the sum of the hydroxyl groups present on the polyol, the isocyanate-reactive group of the monofunctional compound and the isocyanate-reactive groups of the multifunctional compound being from 1.15:1 to 1.35:1.