Emulsifiers and their use in water dispersible polyisocyanate compositions

• US 5,744,542 A
• Filed: 11/06/1996
• Issued: 04/28/1998
• Est. Priority Date: 03/27/1995
• Status: Expired due to Fees

• Current Assignee: PPG Industries Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Incorporated (Nouryon BV)
• Inventors: Martz, Jonathan T., Jennings, Robert E., Donnelly, Karen D., Carney, Joseph M.
• Primary Examiner(s): NILAND, PATRICK DENNIS
• Application Number:
  US08/744,566
• Time in Patent Office: 538 Days
• Field of Search: 524/507, 524/539, 524/591, 524/839, 524/840, 524/590, 525/123, 525/131, 525/455, 528/44, 560/26, 560/115
• US Class Current: 524/590
• CPC Class Codes: C08G 18/283 Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
• CPC Class Codes: C08G 18/2865 Compounds having only one primary or secondary amino group; Ammonia
• CPC Class Codes: C08G 18/6254 Polymers of alpha-beta ethylenically unsaturated carboxylic acids and of esters of these acids containing hydroxy groups
• CPC Class Codes: C08G 18/6283 Polymers of nitrogen containing compounds having carbon-to-carbon double bonds C08G18/6262, C08G18/6266 take precedence
• CPC Class Codes: C08G 18/706 the liquid medium being water
• CPC Class Codes: C09D 175/04 Polyurethanes

Abstract

An aqueous two-component polyisocyanate coating composition is based on an essentially isocyanate-free emulsifier that comprises the reaction product of:

(i) an isocyanate and

(ii) a member selected from the group consisting of: hydroxy functional polyalkyl ethers containing at least five ethylene oxide, alcohols different from said polyalkyl ethers, amine compounds, and combinations thereof. The hydroxy functional polyalkyl ether is provided in a quantity sufficient to react at least one equivalent of isocyanate groups in polyisocyanate (i), and the total amounts of reactants (ii) are sufficient to react all of the isocyanate groups of the polyisocyanate (i).

Claims

1. An emulsifier having a number average molecular weight ranging from about 1000 to about 4000, said emulsifier comprising the reaction product of:

(a) an isocyanate component comprising an isocyanate oligomer having at least two free isocyanate groups, and

(b) a hydroxy functional polyalkyl ether component present in an amount sufficient to react with all of the isocyanate oligomer'"'"'s free isocyanate groups, said hydroxy functional polyalkyl ether component comprising at least one mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups.

7. The emulsifier of claim 1 wherein the isocyanate oligomer is an isocyanurate.

8. The emulsifier of claim 7 where in the isocyanurate is based on isophorone diisocyanate.

9. The emulsifier of claim 1 wherein the hydroxy functional polyalkyl ether component consists essentially of said mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups.

2. An emulsifier having a number average molecular weight ranging from about 1000 to about 4000, said emulsifier comprising the reaction product of:

(a) an isocyanate component comprising an isocyanate oligomer having at least two free isocyanate group, and

(b) a defunctionalizing component present in an amount sufficient to react with all of the isocyanate oligomer'"'"'s free isocyanate groups, said defunctionalizing component comprising;

(i) a mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups, wherein said mono-hydroxy functional polyalkyl ether is present in an amount sufficient to react with at least one equivalent of the isocyanate oligomer'"'"'s isocyanate groups, and

(ii) at least one reactant selected from the group consisting of;

a. mono-hydroxy functional alcohols,

b. mono-hydroxy functional glycol ethers different from said mono-hydroxy functional polyalkyl ethers, and

c. amine compounds having an active amine hydrogen reactive with at least one equivalent of the isocyanate oligomer'"'"'s free isocyanate groups.

10. The emulsifier of claim 2 wherein the defunctionalizing component consists essentially of said mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups and at least one reactant selected from the group consisting of:

(a) mono-hydroxy functional alcohols, and

(b) mono-hydroxy functional glycol ethers different from said mono-hydroxy functional polyalkyl ethers.

11. The emulsifier of claim 2 wherein the defunctionalizing component comprises said mono-hydroxy functional polyalkyl ether containing at least five ethylene oxide groups;

and at least two reactants selected from the group consisting of;

(a) a mono-hydroxy functional alcohol;

(b) a mono-hydroxy functional glycol ether different from said mono-hydroxy functional polyalkyl ethers; and

(c) an amine compound having an active amine hydrogen reactive with at least one equivalent of the isocyanate oligomer'"'"'s free isocyanate groups.

3. A water dispersible polyisocyanate composition, said water dispersible polyisocyanate composition comprising:

(a) a first isocyanate component comprising a first isocyanate oligomer having at least two free isocyanate groups, and

(b) an emulsifier component having a number average molecular weight ranging from about 1000 to about 4000, said emulsifier comprising the reaction product of;

(i) a second isocyanate component comprising a second isocyanate oligomer having at least two free isocyanate groups, and

(ii) a hydroxy functional polyalkyl ether component present in an amount sufficient to react with all of the second isocyanate oligomer'"'"'s free isocyanate groups, said hydroxy functional polyalkyl ether component comprising at least one mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups.

12. The polyisocyanate composition of claim 3 wherein the first isocyanate component is a biuret.

13. The polyisocyanate composition of claim 3 wherein the first isocyanate component is an isocyanurate.

14. The polyisocyanate composition of claim 13 wherein the isocyanurate is based on isophorone diisocyanate.

15. The polyisocyanate composition of claim 3 wherein the first isocyanate component is an isocyanurate.

16. The polyisocyanate composition of claim 15 wherein the isocyanurate is based on isophorone diisocyanate.

20. The polyisocyanate composition of claim 3 wherein the emulsifier component is present in an amount of from 15 to 40 percent, based on the total weight of the first isocyanate component and the emulsifier component.

4. A water dispersible polyisocyanate composition, said water dispersible polyisocyanate composition comprising:

(a) a first isocyanate component comprising a first isocyanate oligomer having at least two free isocyanate groups, and

(b) an emulsifier component having a number average molecular weight ranging from about 1000 to about 4000, said emulsifier comprising the reaction product of;

(i) a second isocyanate component comprising a second isocyanate oligomer having at least two free isocyanate group, and

(ii) a defunctionalizing component present in an amount sufficient to react with all of the second isocyanate oligomer'"'"'s free isocyanate groups, said defunctionalizing component comprising;

a. a mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups, wherein said mono-hydroxy functional polyalkyl ether is present in an amount sufficient to react with at least one equivalent of the second isocyanate oligomer'"'"'s isocyanate groups, and

b. at least one reactant selected from the group consisting of;

i. mono-hydroxy functional alcohols,

ii. mono-hydroxy functional glycol ethers different from said mono-hydroxy functional polyalkyl ethers, and

iii. amine compounds having an active amine hydrogen reactive with at least one equivalent of the second isocyanate oligomer'"'"'s free isocyanate groups.

17. The polyisocyanate composition of claim 4 wherein the defunctionalizing component consists essentially of said mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups.

18. The polyisocyanate composition of claim 4 wherein the defunctionalizing component consists essentially of said mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups and at least one reactant selected from the group consisting of:

(a) mono-hydroxy functional alcohols, and

(b) mono-hydroxy functional glycol ethers different from said mono-hydroxy functional polyalkyl ethers.

19. The polyisocyanate composition of claim 4 wherein the defunctionalizing component comprises said mono-hydroxy functional polyalkyl ether containing at least five ethylene oxide groups;

and at least two reactants selected from the group consisting of;

(a) a mono-hydroxy functional alcohol;

(b) a mono-hydroxy functional glycol ether different from said mono-hydroxy functional polyalkyl ethers; and

(c) an amine compound having an active amine hydrogen reactive with at least one equivalent of the isocyanate oligomer'"'"'s free isocyanate groups.

5. An aqueous two-component coating composition comprising:

(a) a water dispersible polyisocyanate composition, wherein said water dispersible polyisocyanate composition comprises;

(i) a first isocyanate component comprising a first isocyanate oligomer having at least two free isocyanate groups, and

(ii) an emulsifier component having a number average molecular weight ranging from about 1000 to about 4000, said emulsifier comprising the reaction product of;

a. a second isocyanate component comprising a second isocyanate oligomer having at least two free isocyanate groups, and

b. a hydroxy functional polyalkyl ether component present in an amount sufficient to react with all of the second isocyanate oligomer'"'"'s free isocyanate groups, said hydroxy functional polyalkyl ether component comprising at least one mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups; and

(b) an aqueous polymer resin that contains isocyanate-reactive groups, wherein the water dispersible polyisocyanate composition and the aqueous polymer resin are present in the two-component coating composition in an amount sufficient to provide an equivalent ratio of isocyanate groups to isocyanate-reactive groups in the aqueous polymer resin of 0.5;

1 to 5;

1.

21. The two-component coating composition of claim 5 wherein the first isocyanate component is a biuret.

22. The coating composition of claim 5 wherein the first isocyanate component is an isocyanurate.

23. The coating composition of claim 22 wherein the isocyanurate is based on isophorone diisocyanate.

27. The coating composition of claim 5 wherein the emulsifier component is present in an amount of from 15 to 40 percent, based on the total weight of the first isocyanate component and the emulsifier component.

28. The coating composition of claim 5 wherein the aqueous polymer resin is an acrylic polymer having amine functionality.

29. The coating composition of claim 5 wherein the polyisocyanate composition and the aqueous polymer resin are present in an amount sufficient to provide an equivalent ratio of isocyanate groups in the first isocyanate component to isocyanate-reactive groups in the aqueous polymer resin of about 0.8:

1 to 2;

1.

6. An aqueous two-component coating composition comprising:

(a) a water dispersible polyisocyanate composition, wherein said water dispersible polyisocyanate composition comprises;

(i) a first isocyanate component comprising a first isocyanate oligomer having at least two free isocyanate groups, and

(ii) an emulsifier component having a number average molecular weight ranging from about 1000 to about 4000, said emulsifier comprising the reaction product of;

a. a second isocyanate component comprising a second isocyanate oligomer having at least two free isocyanate group, and

b. a defunctionalizing component present in an amount sufficient to react with all of the second isocyanate oligomer'"'"'s free isocyanate groups, said defunctionalizing component comprising;

i. a mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups, wherein said mono-hydroxy functional polyalkyl ether is present in an amount sufficient to react with at least one equivalent of the second isocyanate oligomer'"'"'s isocyanate groups, and

ii. at least one reactant selected from the group consisting of;

a) mono-hydroxy functional alcohols,

b) mono-hydroxy functional glycol ethers different from said mono-hydroxy functional polyalkyl ethers, and

c) amine compounds having an active amine hydrogen reactive with at least one equivalent of the second isocyanate oligomer'"'"'s free isocyanate groups; and

(b) an aqueous polymer resin that contains isocyanate-reactive groups, wherein the water dispersible polyisocyanate composition and the aqueous polymer resin are present in the two-component coating composition in an amount sufficient to provide an equivalent ratio of isocyanate groups to isocyanate-reactive groups in the aqueous polymer resin of 0.5;

1 to 5;

1.

24. The coating composition of claim 6 wherein the defunctionalizing component consists essentially of said mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups.

25. The coating composition of claim 6 wherein the defunctionalizing component consists essentially of said mono-hydroxy functional polyalkyl ethers containing at least five ethylene oxide groups and at least one reactant selected from the group consisting of:

(a) mono-hydroxy functional alcohols, and

(b) mono-hydroxy functional glycol ethers different from said mono-hydroxy functional polyalkyl ethers.

26. The coating composition of claim 6 wherein the defunctionalizing component comprises said mono-hydroxy functional polyalkyl ether containing at least five ethylene oxide groups;

and at least two reactants selected from the group consisting of;

(a) a mono-hydroxy functional alcohol;

(b) a mono-hydroxy functional glycol ether different from said mono-hydroxy functional polyalkyl ethers; and

(c) an amine compound having an active amine hydrogen reactive with at least one equivalent of the isocyanate oligomer'"'"'s free isocyanate groups.