Coating agent composition and use thereof
View Patent ↗The invention relates to a coating agent composition comprising an isocyanate-group-containing prepolymer obtained by reacting a polyol comprising a polyoxyalkylene polyol having 2-4 hydroxyl groups on average, an oxyethylene group content of 85-100% by mass based on all oxyalkylene groups (100% by mass), and an arithmetic-average molecular weight of 800-2,500 with an alicyclic isocyanate and/or an aliphatic isocyanate in the presence of an organic acid bismuth salt catalyst, the isocyanate(s) being used in such an amount as to result in an isocyanate index of 150-300. The invention can provide a coating agent composition which forms a coating film or film having moisture permeability, excellent in mechanical properties and yellowing resistance, having laundering durability and resistance to sweat deterioration, and containing no organotin compounds.
1. A process of making a coated substrate, comprising: coating a substrate with a coating composition comprising
at least one isocyanate-group-containing prepolymer obtained by reacting
(a) a polyoxyalkylene polyol, with
(b) at least one isocyanate compound comprising an alicyclic isocyanate, an aliphatic isocyanate, or a combination thereof in the presence of an organic acid bismuth salt catalyst,
wherein
said polyoxyalkylene polyol (a) comprises as a mixture:
from 20% by mole to less than 100% by mole of a first polyoxyalkylene polyol having three hydroxyl groups and a hydroxyl-value-converted molecular weight of from 500 to less than 2,000, and
from more than 0% by mole to 80% by mole of a second polyoxyalkylene polyol having three hydroxyl groups and a hydroxyl-value-converted molecular weight of from 2,000 to 5,000, where the percents by mole are relative to 100% by mole of the mixture,
the isocyanate compound is present during said reacting in such an amount as to result in an isocyanate index of 150-300, and
said polyoxyalkylene polyol (a) has an oxyethylene group content of 85-100% by mass based on all oxyalkylene groups thereof (100% by mass); and
curing said coating composition.
2. The process of claim 1 , wherein either of said first and second polyoxyalkylene polyol comprises a polyoxyethylene polyol, a polyoxyethylene-polyoxypropylene polyol, or a combination thereof.
3. The process of claim 1 , wherein said isocyanate compound comprises isophorone diisocyanate.
4. The process of claim 1 , wherein said organic acid bismuth salt catalyst comprises a bismuth salt of an aliphatic carboxylic acid having 6-20 carbon atoms.
5. The process of claim 4 , wherein the organic acid bismuth salt catalyst comprises at least one member selected from the group consisting of a bismuth salt of octylic acid, a bismuth salt of neodecanoic acid, and a bismuth salt of neododecanoic acid.
6. The process of claim 1 , wherein the organic acid bismuth salt catalyst is present in an amount of 5-100 ppm relative to the total amount of all polyols and the isocyanate compound during said reacting.
7. An article having a coating film obtained from the process of claim 1 .
8. A film obtained from the process of claim 1 .
9. The process of claim 1 , wherein said reacting occurs at a temperature from 40 to 150° C.
10. The process of claim 1 , wherein said alicyclic isocyanate compound comprises at least one member selected from the group consisting of isophorone diisocyanate, 4,4′-dicyclohexylmethane diisocyanate, 2,5-norbornane diisocyanate, 2,6-norbornane diisocyanate, and a mixture of 2,5-norbornane diisocyanate and 2,6-norbornane diisocyanate.
11. The process of claim 1 , wherein said aliphatic isocyanate compound comprises at least one member selected from the group consisting of 1,6-hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, lysine diisocyanate, and lysine triisocyanate.
12. The process of claim 1 , wherein said polyoxyalkylene polyol (a) consists of from 20% by mole to less than 100% by mole of said first polyoxyalkylene polyol (having three hydroxyl groups and a hydroxyl-value-converted molecular weight of from 500 to less than 2,000), and
from more than 0% by mole to 80% by mole of said second polyoxyalkylene polyol (having three hydroxyl groups and a hydroxyl-value-converted molecular weight of from 2,000 to 5,000).
13. The method according to claim 1 , wherein said contacting occurs at a temperature of 20° C. for a period of five days and at a relative humidity of 60%.
14. The process of claim 1 , wherein said polyoxyalkylene polyol (a) comprises:
from 50% by mole to 90% by mole of said first polyoxyalkylene polyol (having three hydroxyl groups and a hydroxyl-value-converted molecular weight of from 500 to less than 2,000), and
from 10% by mole to 50% by mole of said second polyoxyalkylene polyol (having three hydroxyl groups and a hydroxyl-value-converted molecular weight of from 2,000 to 5,000).
15. The process according to claim 1 , wherein said at least one isocyanate compound comprises 2,5-norbornane diisocyanate; 2,6-norbornane diisocyanate; a mixture of 2,5-norbornane diisocyanate and 2,6-norbornane diisocyanate; 1,6-hexamethylene diisocyanate; 2,2,4-trimethyhexamethylene diisocyanate; lysine diisocyanate and lysine triisocyanate.
16. The process of claim 1 , wherein said alicyclic isocyanate compound comprises at least one member selected from the group consisting of 4,4′-dicyclohexylmethane diisocyanate, 2,5-norbornane diisocyanate, 2,6-norbornane diisocyanate, and a mixture of 2,5-norbornane diisocyanate and 2,6-norbornane diisocyanate.
17. The process of claim 1 , wherein said curing comprises contacting said coating composition with moisture, thereby curing said coating composition.
18. The process of claim 17 , further comprising stripping the cured composition from the substrate.
19. The process of claim 1 , wherein said curing comprises contacting said coating composition with a polyamine vapor, thereby curing said coating composition.
20. The process of claim 19 , further comprising stripping the cured composition from the substrate.