Isocyanurate polyisocyanate and its use as a curing agent for a two-component polyurethane composition

• US 4,801,663 A
• Filed: 03/29/1988
• Issued: 01/31/1989
• Est. Priority Date: 04/03/1987
• Status: Expired due to Term

• Current Assignee: Asahi Kasei Kogyo Kabushiki Kaisha (Asahi Kasei Corporation)
• Original Assignee: Asahi Kasei Kogyo Kabushiki Kaisha (Asahi Kasei Corporation)
• Inventors: Asahina, Yoshiyuki, Ueyanagi, Kaoru, Oyabu, Norio
• Primary Examiner(s): Welsh, Maurice J.
• Application Number:
  US07/174,919
• Time in Patent Office: 308 Days
• Field of Search: 528/73, 252/182.21, 525/528
• US Class Current: 525/528
• CPC Class Codes: C07D 251/34 Cyanuric or isocyanuric esters
• CPC Class Codes: C08G 18/1875 containing ammonium salts or mixtures of secondary of tertiary amines and acids
• CPC Class Codes: C08G 18/6225 Polymers of esters of acrylic or methacrylic acid
• CPC Class Codes: C08G 18/792 formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
• CPC Class Codes: C08G 18/798 containing urethdione groups
• CPC Class Codes: C09D 175/04 Polyurethanes

Abstract

A novel isocyanurate polyisocyanate is disclosed containing N,N'"'"',N"-tris(6-isocyanatohexyl)-isocyanurate in an extremely high proportion and having an extremely low viscosity. The novel isocyanurate polyisocyanate is excellent not only in compatibility with a polyol having a low polarity but also in solubility in a solvent having a low polarity as well as in a polar solvent. The novel isocyanurate polyisocyanate is very useful as a curing agent for a two-component polyurethane composition, especially a two-component polyurethane coating composition. The two-component polyurethane coating composition of the present invention is capable of providing a coat film having extremely excellent properties.

Claims

1. An isocyanurate polyisocyanate comprising:

(a) at least 60% by weight, based on the total weight of the components (a), (b) and (c), of N,N'"'"',N"-tris(6-isocyanatohexyl)-isocyanurate,

(b) from 0 to 10% by weight, based on the total weight of the components (a), (b) and (c), of N,N'"'"'-bis(6-isocyanatohexyl)-uretodione, and

(c) 40% by weight or less, based on the total weight

of the components (a), (b) and (c), of poly(6-isocyanatohexyl)-isocyanurate,

said polyisocyanate having a viscosity of 1600 cps or less as measured at 25°

C.

2. The isocyanurate polyisocyanate according to claim 1, wherein the weight proportion of N,N'"'"',N"-tris(6-isocyanatohexyl)-isocyanurate (a) relative to the components (a), (b) and (c) is from 60 to 95%, and the weight proportion of poly(6-isocyanatohexyl)-isocyanurate relative to the components (a), (b) and (c) is from 5 to 40%.

3. The isocyanurate polyisocyanate according to claim 1 or 2, having a viscosity of from 400 to 1500 cps as measured at 25°

C.

4. The isocyanurate polyisocyanate according to claim 1 or 2, having a viscosity of from 400 to 1400 cps as measured at 25°

C.

5. The isocyanurate polyisocyanate according to claim 1 or 2, having a viscosity of from 400 to 1300 cps as measured at 25°

C.

6. A method for curing a polyol, which comprises mixing a polyol having at least 2 hydroxyl groups with an isocyanurate polyisocyanate comprising:

(a) at least 60% by weight, based on the total weight hBbK of the components (a), (b) and (c), of N,N'"'"',N"-tris(6-isocyanatohexyl)-isocyanurate,

(b) from 0 to 10% by weight, based on the total weight of the components (a), (b) and (c), of N,N'"'"'-bis(6-isocyanatohexyl)-uretodione, and

(c) 40% by weight or less, based on the total weight of the components (a), (b) and (c), of poly(6-isocyanatohexyl)-isocyanurate,

said polyisocyanate having a viscosity of 1600 cps or less as measured at 25°

C.,

said polyisocyanate being employed in an amount such that the equivalent ratio of the isocyanate groups in said polyisocyanate to the hydroxyl groups in said polyol is from 1;

5 to 2;

1.

7. The method according to claim 6, wherein the weight proportion of N,N'"'"',N"-tris(6-isocyanatohexyl)-isocyanurate (a) relative to the components (a), (b) and (c) is from 60 to 95%, and the weight proportion of poly(6-isocyanatohexyl)-isocyanurate relative to the components (a), (b) and (c) is from 5 to 40%.

8. The metod according to claim 6 or 7, wherein said isocyanurate polyisocyanate has a viscosity of from 400 to 1500 cps as measured at 25°

C.

9. The method according to claim 6 or 7, wherein said isocyanurate polyisocyanate has a viscosity of from 400 to 1400 cps as measured at 25°

C.

10. The method according to claim 6 or 7, wherein said isocyanurate polyisocyanate has a viscosity of from 400 to 1300 cps as measured at 25°

C.

11. The method according to claim 6 or 7, wherein said polyol is at least one member selected from the group consisting of an aliphatic hydrocarbon polyol, a polyether polyol, a polyester polyol, a polycarbonate polyol, an epoxy resin, an acrylic polyol and a fluorine-containing polyol.

12. A two-component polyurethane coating composition comprising:

(A) an isocyanurate polyisocyanate comprising;

(a) at least 60% by weight, based on the total weight of the components (a), (b) and (c), of N,N'"'"',N"-tris(6-isocyanatohexyl)-isocyanurate,

(b) from 0 to 10% by weight, based on the total weight of the components (a), (b) and (c), of N,N'"'"'-bis(6-isocyanatohexyl)-uretodione, and

(c) 40% by weight or less, based on the total weight of the components (a), (b) and (c), of poly(6-isocyanatohexyl)-isocyanurate,

said polyisocyanate having a viscosity of 1600 cps or less as measured at 25°

C., and

(B) a polyol having at least 2 hydroxyl groups in one molecule, wherein the equivalent ratio of the isocyanate groups in the component (A) to the hydroxyl groups in the component (B) is from 1;

5 to 2;

1 and wherein the components (A) and (B) are separately provided and adapted to be mixed in use.

13. The two-component polyurethane coating composition according to claim 12, wherein the weight proportion of N,N'"'"',N"-tris(6-isocyanatohexyl)-isocyanurate (a) relative to the components (a), (b) and (c) is from 60 to 95%, and the weight proportion of poly(6-isocyanatohexyl)-isocyanurate relative to the components (a), (b) and (c) is from 5 to 40%.

14. The two-component polyurethane coating composition according to claim 12 or 13, wherein said isocyanurate polyisocyanate has a viscosity of from 400 to 1500 cps as measured at 25°

C.

15. The two-component polyurethane coating composition according to claim 12 or 13, wherein said isocyanurate polyisocyanate has a viscosity of from 400 to 1400 cps as measured at 25°

C.

16. The two-component polyurethane coating composition according to claim 12 or 13, wherein said isocyanurate polyisocyanate has a viscosity of from 400 to 1300 cps as measured at 25°

C.

17. The two-component polyurethane coating composition according to claim 12, wherein said polyol is at least one member selected from the group consisting of an aliphatic hydrocarbon polyol, a polyether polyl, a polyester polyol, a polycarbonate polyol, an epoxy resin, an acrylic polyol and a fluorine-containing polyol.